[ CAS No. 4755-77-5 ] {[proInfo.proName]}

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Quality Control of [ 4755-77-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 4755-77-5 ]

SDS Specification

Alternatived Products of [ 4755-77-5 ]

Product Details of [ 4755-77-5 ]

CAS No. :	4755-77-5	MDL No. :	MFCD00000706
Formula :	C₄H₅ClO₃	Boiling Point :	-
Linear Structure Formula :	C₂H₅OC(O)C(O)Cl	InChI Key :	OWZFULPEVHKEKS-UHFFFAOYSA-N
M.W :	136.53	Pubchem ID :	20884
Synonyms :

Calculated chemistry of [ 4755-77-5 ] Expand+

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.5
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	27.62
TPSA :	43.37 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.12 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.49
Log Po/w (XLOGP3) :	1.43
Log Po/w (WLOGP) :	0.31
Log Po/w (MLOGP) :	-0.09
Log Po/w (SILICOS-IT) :	0.64
Consensus Log Po/w :	0.76

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.39
Solubility :	5.57 mg/ml ; 0.0408 mol/l
Class :	Very soluble
Log S (Ali) :	-1.95
Solubility :	1.55 mg/ml ; 0.0113 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.9
Solubility :	17.4 mg/ml ; 0.127 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.65

Safety of [ 4755-77-5 ]

Signal Word:	Danger	Class:	8,3
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	2920
Hazard Statements:	H226-H314	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 4755-77-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 4755-77-5 ]
Downstream synthetic route of [ 4755-77-5 ]

[ 4755-77-5 ] Synthesis Path-Upstream 1~3

1
[ 79-19-6 ]
[ 4755-77-5 ]
[ 64837-53-2 ]

Yield	Reaction Conditions	Operation in experiment
24%	at 70℃; for 5 h;	Step 1 ethyl 5-amino-l,3,4-thiadiazole-2-carboxylate To a solution of hydrazinecarbothioamide (10 g, 54.8 mmol) in POCI₃ (25 mL) was added ethyl 2-chloro-2-oxacetate (6.1 mL, 54.8 mmol). The reaction was heated to 70°C and stirred for 5 h. POCI₃ was completely removed from the reaction mixture under vacuum. The residue was diluted with ice cold water (150 mL) and basified to pH 8 with saturated sodium bicarbonate solution and then extracted with ethyl acetate (200 mL). The organic layer was separated and dried over a₂S0₄, and the solvent was evaporated to obtain crude product. The crude product was purified by flash chromatography (silica gel 100-200?, 2percent methanol and dichloromethane) to afford ethyl 5-amino-l,3,4-thiadiazole-2-carboxylate as a yellow solid (3.1 g, 24percent yield). ? NMR (400 MHz, DMSO-d₆): ? 7.94 (s, 2H), 4.29 (q, 2H), 1.27 (t, 3H); LC- MS m/z calcd for [M+H]⁺ 174.03, found 174.1.

Reference： [1] Patent: WO2013/49565, 2013, A1, . Location in patent: Page/Page column 68
[2] Annali di Chimica (Rome, Italy), 1959, vol. 49, p. 2124,2131
[3] Patent: WO2007/38865, 2007, A1, . Location in patent: Page/Page column 47

2
[ 623-33-6 ]
[ 4755-77-5 ]
[ 29655-79-6 ]

Yield	Reaction Conditions	Operation in experiment
51%	With triethylamine In dichloromethane	Example 2 Ii; Compound 4 was prepared according to the Ref: J. Hetero. Chem. 1995, 32, 1693-1702. Then, it was reduced by NaBH₄ZLiCl in ethanol solution. Further oxidation by Dess-Martin reagent gave the desired aldehyde 6 in 25 percent overall two-step yield.

Reference： [1] Synthetic Communications, 2000, vol. 30, # 17, p. 3171 - 3180
[2] Patent: WO2007/124546, 2007, A1, . Location in patent: Page/Page column 63
[3] Chemische Berichte, 1897, vol. 30, p. 590
[4] Journal of the American Chemical Society, 1997, vol. 119, # 1, p. 86 - 93
[5] Organic Process Research and Development, 2004, vol. 8, # 2, p. 192 - 200

3
[ 4755-77-5 ]
[ 29655-79-6 ]

Reference： [1] Patent: US2002/35115, 2002, A1,

[ 4755-77-5 ] Synthesis Path-Downstream 1~15

1
[ 79-19-6 ]
[ 4755-77-5 ]
[ 64837-53-2 ]

Yield	Reaction Conditions	Operation in experiment
24%	With trichlorophosphate; at 70℃; for 5h;	Step 1 ethyl 5-amino-l,3,4-thiadiazole-2-carboxylate To a solution of hydrazinecarbothioamide (10 g, 54.8 mmol) in POCI3 (25 mL) was added ethyl 2-chloro-2-oxacetate (6.1 mL, 54.8 mmol). The reaction was heated to 70°C and stirred for 5 h. POCI3 was completely removed from the reaction mixture under vacuum. The residue was diluted with ice cold water (150 mL) and basified to pH 8 with saturated sodium bicarbonate solution and then extracted with ethyl acetate (200 mL). The organic layer was separated and dried over a2S04, and the solvent was evaporated to obtain crude product. The crude product was purified by flash chromatography (silica gel 100-200?, 2percent methanol and dichloromethane) to afford ethyl 5-amino-l,3,4-thiadiazole-2-carboxylate as a yellow solid (3.1 g, 24percent yield). ? NMR (400 MHz, DMSO-d6): ? 7.94 (s, 2H), 4.29 (q, 2H), 1.27 (t, 3H); LC- MS m/z calcd for [M+H]+ 174.03, found 174.1.
	at 160℃; for 5h;	EXAMPLE 67-( { [5-( 1 -Ethyl- 1 -hvdroxypropyl)- 1.3.4-thiadiazol-2-yl]amino 1 methyl)-4-phenylquinoline-2-carbonitrile Step 1: Ethyl 5-amino-1.3.4-thiadiazole-2-carboxylateN-NQ S NH,EtOA mixture of ethyl chloro(oxo)acetate (0.5 g, 3.68 mmol) and hydrazinecarbothioamide (0.335 g, 3.68 mmol) was heated to 160° C for 5 h. The solvent was removed under reduce pressure and the crude purified on silica gel (eluting with 3percent methanol in DCM) to give the title product. 1H NMR (400 MHz, acetone-ds): delta 7.28 (bs, IH), 9.67 (bs, IH), 4.39 (q, 2H), 1.38 (t, 3H).

Reference： [1]Patent: WO2013/49565,2013,A1 .Location in patent: Page/Page column 68
[2]Annali di Chimica,1959,vol. 49,p. 2124,2131
[3]Patent: WO2007/38865,2007,A1 .Location in patent: Page/Page column 47

2
[ 16313-65-8 ]
[ 4755-77-5 ]
[ 54166-78-8 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 47 2'-Carbamoyl-4'-nitrooxanilic acid ethyl ester. 59 <strong>[16313-65-8]<strong>[16313-65-8]2-Amino-5-nitrobenzamid</strong>e</strong> (5.43 g. 0.03 mole) is condensed with 3.7 ml (0.033 mole) of ethyl oxalyl chloride in a manner similar to example 3, giving 6.54 g of the title compound, m.p. 206-209 C., after crystallization from ethanol. Elemental Analysis for C11 H11 N3 O6: Calc'd: C, 46.98; H, 3.94; N, 14.94. Found: C, 46.68; H, 3.96; N, 15.12.
		EXAMPLE 30 2'-Carbamoyl-4'-nitrooxanilic acid ethyl ester. 59 <strong>[16313-65-8]<strong>[16313-65-8]2-Amino-5-nitrobenzamid</strong>e</strong> (5.43 g., 0.03 mole) is condensed with 3.7 ml. (0.033 mole) of ethyl oxalyl chloride in a manner similar to example 12, giving 6.54 g. of the title compound, m.p. 206-209 C., after crystallization from ethanol. Elemental Analysis for C11 H11 N3 O6: Calc'd: C, 46.98; H, 3.94; N, 14.94: Found: C, 46,68; H, 3.96; N, 15.12.
		EXAMPLE 30 2'-Carbamoyl-4'-nitrooxanilic acid ethyl ester. 59 <strong>[16313-65-8]<strong>[16313-65-8]2-Amino-5-nitrobenzamid</strong>e</strong> (5.43 g., 0.03 mole) is condensed with 3.7 ml. (0.033 mole) of ethyl oxalyl chloride in a manner similar to example 12, giving 6.54 g. of the title compound, m.p. 206-209 C., after crystallization from ethanol. Elemental Analysis for C11 H11 N3 O6: Calc'd: C, 46.98; H, 3.94; N, 14.94. Found: C, 46,68; H, 3.96; N, 15.12.

		EXAMPLE 30 2'-Carbamyl-4'-nitrooxanilic acid ethyl ester. 59 <strong>[16313-65-8]<strong>[16313-65-8]2-Amino-5-nitrobenzamid</strong>e</strong> (5.43 g., 0.03 mole) is condensed with 3.7 ml. (0.033 mole) of ethyl oxalyl chloride in a manner similar to example 12, giving 6.54 g. of the title compound, m.p. 206-209 C., after crystallization from ethanol. Elemental Analysis for C11 H11 N3 O6: Calc'd: C, 46.98; H, 3.94; N, 14.94. Found: C, 46,68; H, 3.96; N, 15.12.
		EXAMPLE 47 2'-Carbamoyl-4'-nitrooxanilic acid ethyl ester. 59 <strong>[16313-65-8]<strong>[16313-65-8]2-Amino-5-nitrobenzamid</strong>e</strong> (5.43 g, 0.03 mole) is condensed with 3.7 ml (0.033 mole) of ethyl oxalyl chloride in a manner similar to example 3, giving 6.54 g of the title compound, m.p. 206-209 C., after crystallization from ethanol. Elemental Analysis for C11 H11 N3 O6: Calc'd: C, 46.98; H, 3.94; N, 14.94. Found: C, 46.68; H, 3.96; N, 15.12.
	With triethylamine; In tetrahydrofuran; at 0℃; for 1h;	Step 2 To a solution of <strong>[16313-65-8]2-amino-5-nitrobenzamide</strong> (18.1 g) and triethylamine (15 mL) in THF (100 mL) was added dropwise a solution of ethyl chloroglyoxylate (14.4 g) in THF (20 mL) under ice-cooling, and the mixture was stirred at 0C for 1hr. 1N Hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, saturated aqueous sodium hydrogencarbonate and saturated brine, dried, and concentrated. The obtained crude crystals were washed with diisopropyl ether to give ethyl [2-(aminocarbonyl)-4-nitrophenyl]amino}(oxo)acetate (8.1 g). 1H-NMR (300MHz, DMSO-d6) delta: 1.37 (3H, t, J = 7.1 Hz), 3.33 (3H, s), 4.41 (2H, q, J = 7.1 Hz), 8.03 (1H, d, J = 8.8 Hz), 8.59 (1H, dd, J = 8.8, 2.7 Hz), 8.83 (1H, d, J = 2.2 Hz).
8.1 g	With triethylamine; In tetrahydrofuran; at 0℃; for 1h;	Step 2 To a solution of <strong>[16313-65-8]2-amino-5-nitrobenzamide</strong> (18.10 g) and triethylamine (15 ml) in THF (100 mL) was added dropwise a solution of ethyl chloroglyoxylate (14.36 g) in THF (20 ml) under ice-cooling, and the mixture was stirred at 0 C. for 1 hr. 1N Hydrochloric acid was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water, saturated aqueous sodium hydrogen carbonate and saturated brine, dried and concentrated. The obtained crude crystals were washed with diisopropy ether to give ethyl [2-(aminocarbonyl)-4-nitrophenyl]amino}(oxo)acetate (8.1 g). 1H NMR (300 MHz, DMSO-d6) delta: 1.4 (t, J=7.1 Hz, 2H) 3.3 (s, 3H) 4.4 (q, J=7.1 Hz, 2H) 8.0 (d, J=8.8 Hz, 1H) 8.6 (dd, J=8.8, 2.7 Hz, 1H) 8.8 (d, J=2.2 Hz, 1H)
		EXAMPLE 47 2'-Carbamoyl-4'-nitrooxanilic acid ethyl ester. 59 <strong>[16313-65-8]<strong>[16313-65-8]2-Amino-5-nitrobenzamid</strong>e</strong> (5.43 g, 0.03 mole) is condensed with 3.7 ml (0.033 mole) of ethyl oxalyl chloride in a manner similar to example 3, giving 6.54 g of the title compound, m.p. 206-209C., after crystallization from ethanol. Elemental Analysis for C11 H11 N3 O6: Calc'd: C, 46.98; H, 3.94; N, 14.94. Found: 46.68; H, 3.96; N, 15.12.

Reference： [1]Journal of Medicinal Chemistry,1975,vol. 18,p. 926 - 933
[2]Patent: US4054661,1977,A
[3]Patent: US4191840,1980,A
[4]Patent: US4069343,1978,A
[5]Patent: US4154961,1979,A
[6]Patent: US4160100,1979,A
[7]Patent: EP1953148,2008,A1 .Location in patent: Page/Page column 131
[8]Patent: US2015/329556,2015,A1 .Location in patent: Paragraph 1772-1773
[9]Patent: US3966965,1976,A

3
[ 4755-77-5 ]
[ 21344-90-1 ]
N-[4-(2-Chloro-phenyl)-thiazol-2-yl]-oxalamic acid ethyl ester [ No CAS ]

Reference： [1]Arzneimittel-Forschung/Drug Research,1986,vol. 36,p. 1391 - 1393

4
[ 4506-66-5 ]
[ 4755-77-5 ]
[ 235424-22-3 ]

Reference： [1]European Journal of Inorganic Chemistry,1999,p. 1067 - 1071

5
[ 7579-20-6 ]
[ 4755-77-5 ]
3-[(ethyloxy)(oxo)acetyl]amino}pyridine-4-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With pyridine; at 0 - 20℃; for 15h;	Step 1. To a suspension of commercially available 3-aminopyridine-4-carboxylic acid (4.84 g, 35.1 mmol) in pyridine (60 mL) wasadded dropwise ethyl chloroglyoxylate (9.58 g, 70.2 mmol) at 0 C,and the mixture was stirred at room temperature for 15 h. Thereaction mixture was concentrated under reduced pressure andthe residue was suspended with water. The resulting precipitatewas collected by filtration to give 3-(2-ethoxy-2-oxoacetamido)pyridine-4-carboxylic acid as a pale yellow powder (3.74 g,45percent). 1H NMR (200 MHz, DMSO-d6) d 1.33 (3H, t, J = 7.0 Hz), 4.33(2H, q, J = 7.0 Hz), 7.88 (1H, d, J = 5.0 Hz), 8.53 (1H, d, J = 5.0 Hz),9.71 (1H, s), 12.10 (1H, s).
45%	With pyridine; at 35℃; for 15h;Cooling with ice;	Step 2 To a suspension (60 mL) of 3-aminoisonicotinic acid (4.84 g, 35.1 mmol, 100percent) in pyridine was added dropwise ethyl chloroglyoxylate (9.58 g, 70.2 mmol) under ice-cooling, and the mixture was stirred at room temperature for 15 hrs. The reaction mixture was concentrated under reduced pressure and water was added to the concentrated residue to give a suspension. The insoluble material was collected by filtration to give, 3-[(ethyloxy)(oxo)acetyl]amino}pyridine-4-carboxylic acid as a pale-yellow powder (3.74 g, 45percent). 1H-NMR (200 MHz, DMSO-d6) delta: 1.33 (3H, t, J=7.0 Hz), 4.33 (2H, q, J=7.0 Hz), 7.88 (1H, d, J=5.0 Hz), 8.53 (1H, d, J=5.0 Hz), 9.71 (1H, s), 12.10 (1H, s).
	With triethylamine; In tetrahydrofuran; water;	Example 33 3-(Oxalyl-amino)-isonicotinic acid; To a stirred solution of 3-amino-isonicotinic acid (0.5 g, 3.62 mmol) and triethylamine (1 ml) in dry tetrahydrofuran (50 ml) at 0° C. was added dropwise ethyl oxalyl chloride (0.5 g, 3.69 mmol). The resulting reaction mixture was stirred at room temperature for 3 h, filtered and the volatiles were evaporated in vacuo. To the residue was added water (50 ml) and the resulting mixture was extracted with diethyl ether (2*50 ml). The organic phase was washed with saturated aqueous sodium chloride (50 ml), dried (MgSO4), filtered and the solvent evaporated in vacuo affording 0.4 g (46percent) of 3-(ethoxyoxalyl-amino)-isonicotinic acid as a solid.

Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 4443 - 4459
[2]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 5487 - 5505
[3]Patent: US2015/329556,2015,A1 .Location in patent: Paragraph 1618
[4]Patent: US6225329,2001,B1

6
[ 4755-77-5 ]
[ 5271-27-2 ]
[ 960403-77-4 ]

Yield	Reaction Conditions	Operation in experiment
99%	With triethylamine; In dichloromethane;Cooling;	1 -Methyl-3-phenylpiperazine (123.2 g; 0.70 mol) was dissolved in 500 dichloromethane. Triethylamine (30 ml; ca 0.2 mol) was added. A solution of ethyl chlorooxalate (107 g; 0.78 mol) in dichloromethane was slowly added under cooling. At 2/3 of the total addition a thick suspension was formed. Even after addition of more solvent, stirring remained difficult. The mixture was quenched with 10percent sodium carbonate. The organic layer is washed again with carbonate, dried and evaporated to an orange oil (191.2 g; 0.69 mol; 99 percent). Crystallisation with seeding proved difficult. Deep evaporation and storage as oil.TLC: very pure, a small amount of coloured polar material on baseline. No trace of the dioxamide (prepared from oxalylchloride and piperazine). GC: 18.0/18.2 min, 0.36 areapercent of 3.8 min impurity. A small sample (20 g) was stirred with water to induce crystallisation. <n="15"/>mp ca 45 °C. The main bulk of the oil solidified after a few days of standing. Melting was needed before use.

Reference： [1]Patent: WO2007/144409,2007,A1 .Location in patent: Page/Page column 14

7
[ 7664-93-9 ]
[ 2401-21-0 ]
[ 4755-77-5 ]
[ 180868-99-9 ]

Yield	Reaction Conditions	Operation in experiment
	With magnesium; In water; cadmium(II) chloride; benzene;	Method A Grignard reagent was prepared in conventional manner as follows: The dichloroiodobenzene was added to magnesium over 1-2 hours and the resulting solution was refluxed for about 4 hours. As all the Mg had not dissolved the Grignard was allowed to stir at room temperature overnight. The flask was then cooled in ice and the dry cadmium chloride added portionwise over 10 minutes. When all the cadmium chloride had been added the reaction mixture was allowed to warm to room temperature and was then heated under reflux for 45 minutes. The ether was evaporated off and the residue washed twice with dry benzene which, in was turn, also evaporated off. The residue was then taken and treated with ethyl oxalyl chloride in 20 mls dry benzene. This was added slowly from a dropping funnel with stirring. The reaction was very vigorous. When addition was complete and spontaneous reflux had subsided the reaction mixture was refluxed for a further hour. The reaction mixture was then cooled in an ice bath. Ice/water was carefully added. Sufficient 20percent H2 SO4 was then added to give two clear phases. The aqueous phase was separated and extracted twice with benzene. The benzene layers were combined and extracted 1water, 1Na2 CO3 solution, 1water and 1NaCl solution. The benzene solution was then dried over MgSO4, filtered and evaporated down. 17.5 g crude material was obtained. NMR and TLC analyses were performed. TLC in Si/CHCl3 gave two spots, one corresponding to the title compound (product) and one to the dichloroiodobenzene (starting material).

Reference： [1]Patent: US5912345,1999,A

8
Ethyl N-(p-difluoromethylphenyl)oxamide [ No CAS ]
[ 29848-57-5 ]
[ 555-16-8 ]
[ 4755-77-5 ]
1-methyl-7-trifluoromethylquinoxaline-2(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With HF; SF4; nitric acid; acetic anhydride; In ethanol; acetic acid;	Those of the starting materials which are of the formula SPC10 are prepared by the following reaction scheme; SPC11 In a representative preparation, ethyl N-(4-difluoromethyl-2-nitrophenyl)oxamide was prepared as described below. p-Nitrobenzal fluoride (5 grams) (prepared by reaction of p-nitrobenzaldehyde with SF4 /HF) was hydrogenated over 200 mg. platinum oxide in 50 ml. of ethanol. The catalyst was removed by filtration and the ethanol, by evaporation. The residue was dissolved in 50 ml. of cold ether; to this solution was added a solution of ethyl oxalyl chloride (7 ml.) in 25 ml. of ether. The reaction mixture was stirred for 15 minutes, filtered, and evaporated to dryness. The residue, the desired ethyl N-(p-difluoromethylphenyl)oxamide product, was recrystallized from a mixture of ethanol and water, m.p. 110-114C. Ethyl N-(p-difluoromethylphenyl)oxamide (1 gram) was dissolved in 4 ml. of each of acetic acid and acetic anhydride and the mixture cooled to about 0-5C. Fuming nitric acid (1 ml.) mixed with acetic acid (2 ml.) was added portionwise to the cooled solution. An additional 1 ml. of fuming nitric acid was added one hour later. Two hours after the initial addition, the reaction mixture was poured into water, and the ethyl N-(4-difluoromethyl-2-nitrophenyl)oxamide product was collected, washed, and recrystallized from a mixture of ethanol and water, m.p. 113-115C. Those starting materials which are 1-methylquinoxalinones: SPC12 are prepared in accordance with the following procedures SPC13 The following preparation of 1-methyl-7-trifluoromethyl-2(1H)-quinoxalinone illlustrates the procedure.

Reference： [1]Patent: US3962440,1976,A

9
[ 5900-59-4 ]
[ 4755-77-5 ]
[ 1241915-84-3 ]

Yield	Reaction Conditions	Operation in experiment
88%	With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 0 - 20℃;	[00394] Step B: To a solution of <strong>[5900-59-4]2-amino-4-chlorobenzamide</strong> (393 mg, 2.30 mmol) and DIEA (0.60 mL, 3.45 mmol) in THF (15 mL) at 0 0C was added ethyl chlorooxoacetate (0.28 mL, 2.53 mmol). The solution was allowed to warm to rt and stir for 2 h. The mixture was concentrated under reduced pressure and the residue was purified by silica gel chromatography eluting with 10-50percent EtOAc/hexanes to afford ethyl 2-(2-carbamoyl-5-chlorophenylamino)-2-oxoacetate as a solid (545 mg, 88percent). 1H NMR (300 MHz, DMSO-d6) delta 1.32 (t, J= 6.97 Hz, 3 H), 4.31 (q, J= 6.97 Hz, 2 H), 7.34 (d, J= 8.48 Hz, 1 H), 7.86 - 8.03 (m, 2 H), 8.44 (br s, 1 H), 8.62 (s, 1 H), 13.24 (s, 1 H)
88%	With DIEA; In tetrahydrofuran;	Step B:To a solution of <strong>[5900-59-4]2-amino-4-chlorobenzamide</strong> (393 mg, 2.30 mmol) and DIEA (0.60 mL, 3.45 mmol) in THF (15 mL) at 0° C. was added ethyl chlorooxoacetate (0.28 mL, 2.53 mmol).The solution was allowed to warm to room temperature and stir for 2 hrs.The mixture was concentrated under reduced pressure and the residue was purified by silica gel chromatography eluting with 10-50percent EtOAc/hexanes to afford ethyl 2-(2-carbamoyl-5-chlorophenylamino)-2-oxoacetate as a solid (545 mg, 88percent).1H NMR (300 MHz, DMSO-d6) 81.32 (t, J=6.97 Hz, 3H), 4.31 (q, J=6.97 Hz, 2H), 7.34 (d, J=8.48 Hz, 1H), 7.86-8.03 (m, 2H), 8.44 (br s, 1H), 8.62 (s, 1H), 13.24 (s, 1H)

Reference： [1]Patent: WO2010/99379,2010,A1 .Location in patent: Page/Page column 142
[2]Patent: US2012/53176,2012,A1

10
[ 20876-36-2 ]
[ 4755-77-5 ]
[ 496056-18-9 ]

Yield	Reaction Conditions	Operation in experiment
79%	With sodium acetate; acetic acid; at 35 - 90℃; for 1.75h;	General procedure: 6-Amino-3H-1,3-benzoxazol-2-one (700 mg, 4.66 mmol) and sodium acetate (497 mg, 6.05 mmol) were dissolved in acetic acid (20 mL) at 35 °C. Ethyl chlorooxoacetate (677 muL, 6.05 mmol) was added dropwise and the reaction mixture was stirred at 35 °C for 1 h and 45 min at 90 °C then water (50 mL) was added to the solution. The precipitate was filtered, washed with water (2 .x. 30 mL) and dried overnight under vacuum in presence of P2O5 to afford the intermediate ethyl 2-acetamido-N-(2-oxo-3H-1,3-benzoxazol-6-yl)acetate (857 mg, 74percent) as a white solid. A solution of potassium hydroxide (101 mg, 1.80 mmol) in water (400 muL) was added to a suspension of ethyl 2-acetamido-N-(2-oxo-3H-1,3-benzoxazol-6-yl)acetate obtained above (150 mg, 0.60 mmol) in ethanol (3 mL) and the reaction mixture was stirred at room temperature for 2 h. Water (5 mL) was added to the mixture and the resulting homogenous solution was acidified to pH = 1 with concentrated HCl. The precipitate was filtered and dried overnight under vacuum in presence of P2O5 to give 4a (115 mg, 87percent) as a white solid.

Reference： [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 2295 - 2309

11
[ 6086-21-1 ]
[ 4755-77-5 ]
[ 1313739-06-8 ]
C₁₀H₁₄N₆O₃ [ No CAS ]
C₁₄H₁₈N₆O₆ [ No CAS ]

Reference： [1]Synthesis,2011,p. 1633 - 1637

12
[ 4755-77-5 ]
[ 7149-75-9 ]
[ 69066-15-5 ]

Yield	Reaction Conditions	Operation in experiment
96%	With triethylamine; In tetrahydrofuran; at 0 - 20℃; for 6h;	General procedure: To a stirred solution of 3,4-dichloroaniline 4b (1.94?g, 12.0?mmol) in THF (20.0?mL) were added ethyl chloroglyoxylate (1.11?mL, 10.0?mmol) and Et3N (15.2?mL, 11.0?mmol) at 0?°C. The mixture was stirred at room temperature for 6?h. After the precipitate was filtrated off, the filtrate solution was concentrated under reduced pressure. The residue was dissolved in EtOAc, and washed with 1.0?M HCl, saturated NaHCO3 and brine, then dried over MgSO4. Concentration under reduced pressure to provide the title compound 6b (1.58?g, 95percent yield) as white powder, which was used without further purification.

Reference： [1]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 2518 - 2526

13
[ 89283-92-1 ]
[ 4755-77-5 ]
C₉H₈BrClN₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In tetrahydrofuran; at 0 - 20℃; for 1.0h;	5-Bromo-4-chloro-3-aminopyridine (4.1 g, 0.020 mol)Was dissolved in 100 mL of tetrahydrofuran,Triethylamine (2.4 g, 0.024 mol) was added,The system was placed in an ice bath at 0 ° C,A solution of oxalyl chloride monoethyl ester (3.0 g, 0.022 mol)In tetrahydrofuran solution,Reaction at room temperature for 1 hour,Concentrated under reduced pressure,Ethyl acetate (100 mL) was added,Washed with saturated sodium bicarbonate solution (50 mL * 2 times)Dispensing,The organic phase was dried over anhydrous sodium sulfate,Concentrated under reduced pressure to dry,To give 5.5 g of crude solid,Yield 90.0percent.

Reference： [1]Patent: CN106146533,2016,A .Location in patent: Paragraph 0475; 0479; 0480

14
[ 5369-19-7 ]
[ 4755-77-5 ]
C₁₄H₁₉NO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: A mixture of2-(tert-butyl)aniline(15.00 g, 100.52 mmol, 15.63 mL, 1.00eq), Et3N (11.19 g, 110.57 mmol, 15.33 mL, 1.10eq) and DCM (150.00 mL) was stirred at 0 ? 5 °C for 15 minutes; ethyl 2-chloro-2-oxo-acetate (13.72 g, 100.52 mmol, 11.25 mL, 1.00eq) was added to the reaction mixture dropwise during 15 minutes. This mixture was stirred at 20 °C for 16 h. The mixture was quenched with water (100 mL). The mixture was extracted with EtOAc (200 mL * 2). The organic layers was combined, washed with 0.1 M HCl (150 mL) and water (100 mL). The organic phase was dried over Na2SO4, filtered and concentrated by vacuum to give ethyl 2-(2-tert-butylanilino)-2-oxo-acetate (25.00 g, crude) as a colorless oil. A mixture of ethyl 2-(2-tert-butylanilino)-2-oxo-acetate (25.00 g, 100.28 mmol, 1.00eq) and 1,4-dioxane (250.00 mL) was stirred at 20 °C for 5 minutes. A solution of LiOH·H2O (4.21 g, 100.28 mmol, 2.79 mL, 1.00eq) in Water (125.00 mL) was added to the mixtue. The reaction mixture was stirred at rt for 1.5 h. 400 mL water was added the reaction mixture ,the mixture was washed with 300 mL EtOAc. The aqueous layer was adjusted pH to 2 by HCl (12 M), then, extracted with EtOAc (300 mL * 2). The organic layers was combined, washed with 200 mL water. The organic layer was dried, filtered and the filtrate was concentrated by vacuum to give2-((2-(tert-butyl)phenyl)amino)-2-oxoacetic acid (14)(21.00 g, 94.92 mmol, 95percent yield) as a white solid.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 1874 - 1878

15
[ 445-14-7 ]
[ 4755-77-5 ]
C₁₁H₉ClF₃NO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With triethylamine; In dichloromethane; at 0 - 15℃; for 16h;	Compound 88-a (1.00 g, 5.11 mmol, 1.00 eq) was dissolved in dichloromethane (25.00 mL), and triethylamine (1.03 g, 10.22 mmol, 1.42 mL, 2.00 eq) and compound 1-b (837.74 mg, 6.13 mmol, 686.67 mL, 1.20 eq) were successively added to the above solution at 0°C. The reaction solution was maintained at 15°C and stirred for 16 hours. After the reaction was completed, the reaction solution was added with water (100 mL), and extracted with dichloromethane (100 mL 3 3). The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated to give a crude product. The crude product was subjected to column chromatography (petroleum ether : ethyl acetate = 1:0?9:1) to give the product of compound 88-b (1.07 g, yield: 60percent) as a colorless oil. 1H NMR (400 MHz, CHLOROFORM-d) delta=9.39 (br. s., 1H), 8.48 (s, 1H), 7.59 (d, J=8.53 Hz, 1H), 7.30 (s, 1H), 4.46 (q, J=7.03 Hz, 2H), 1.45 (t, J=7.15 Hz, 3H).

Reference： [1]Patent: EP3456711,2019,A1 .Location in patent: Paragraph 0601; 0602

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Technical Information

? Acyl Group Substitution ? Bouveault-Blanc Reduction ? Catalytic Hydrogenation ? Complex Metal Hydride Reductions ? Ester Cleavage ? Hydride Reductions ? Preparation of Aldehydes and Ketones ? Reactions of Amines ? Reactions with Organometallic Reagents ? Rosenmund Reduction ? Specialized Acylation Reagents-Carbodiimides and Related Reagents ? Specialized Acylation Reagents-Ketenes

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Ghs Precautionary Statements

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
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P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ CAS No. 4755-77-5 ] {[proInfo.proName]}

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