[ CAS No. 74974-54-2 ] {[proInfo.proName]}

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Quality Control of [ 74974-54-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 74974-54-2 ]

SDS Specification

Alternatived Products of [ 74974-54-2 ]

Product Details of [ 74974-54-2 ]

CAS No. :	74974-54-2	MDL No. :	MFCD00216629
Formula :	C₅H₁₁ClO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NPEIUNVTLXEOLT-UHFFFAOYSA-N
M.W :	154.59	Pubchem ID :	144702
Synonyms :

Safety of [ 74974-54-2 ]

Signal Word:	Danger	Class:	3
Precautionary Statements:	P210-P403+P235	UN#:	1993
Hazard Statements:	H225	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 74974-54-2 ]

* 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 [ 74974-54-2 ]
Downstream synthetic route of [ 74974-54-2 ]

[ 74974-54-2 ] Synthesis Path-Upstream 1~3

1
[ 563-41-7 ]
[ 74974-54-2 ]
[ 252742-72-6 ]

Yield	Reaction Conditions	Operation in experiment
62%	at 20℃;	4.0 g Semicarbazide hydrochloride, 9.67 mL 2-chloro-1,1,1-trimethoxyethane and 40 mL methanol were combined and stirred at ambient temperature for 3 d. After this time additional 3.5 mL 2-chloro-1,1,1-trimethoxyethane was added to complete the reaction. The mixture was then concentrated under reduced pressure and the crude product was partitioned between ethyl acetate and 1N hydrochloric acid. The organic phase separated and it was washed with additional 1N hydrochloric acid (.x.2). The combined aqueous extracts were extracted with ethyl acetate (.x.5) and all of the organic fraction were then combined, dried over sodium sulfate, filtered and the filtrate was concentrated under reduced pressure. The solid that remained was triturated with ethyl acetate to give the title compound which was used without further purification.Yield: 2.97g (62percent of theory)Analysis: ¹H NMR (500 MHz, dimethyl sulfoxide-d6) in ppm 4.49 (2H, s), 11.55 (1H, br. s.), 11.70 (1H, br. s.)

Reference： [1] Tetrahedron Letters, 2000, vol. 41, # 44, p. 8661 - 8664
[2] Patent: US2012/28939, 2012, A1, . Location in patent: Page/Page column 27
[3] Patent: WO2011/92128, 2011, A1, . Location in patent: Page/Page column 51-52
[4] Patent: WO2014/139328, 2014, A1, . Location in patent: Page/Page column 614
[5] Patent: WO2006/133426, 2006, A2, . Location in patent: Page/Page column 276

2
[ 74974-54-2 ]
[ 252742-72-6 ]

Reference： [1] Patent: US2003/187274, 2003, A1,

3
[ 4426-72-6 ]
[ 74974-54-2 ]
[ 252742-72-6 ]

Reference： [1] Patent: WO2009/67233, 2009, A1, . Location in patent: Page/Page column 69

[ 74974-54-2 ] Synthesis Path-Downstream 1~5

1
[ 563-41-7 ]
[ 74974-54-2 ]
[ 252742-72-6 ]

Yield	Reaction Conditions	Operation in experiment
62%	In methanol; at 20℃;	4.0 g Semicarbazide hydrochloride, 9.67 mL 2-chloro-1,1,1-trimethoxyethane and 40 mL methanol were combined and stirred at ambient temperature for 3 d. After this time additional 3.5 mL 2-chloro-1,1,1-trimethoxyethane was added to complete the reaction. The mixture was then concentrated under reduced pressure and the crude product was partitioned between ethyl acetate and 1N hydrochloric acid. The organic phase separated and it was washed with additional 1N hydrochloric acid (.x.2). The combined aqueous extracts were extracted with ethyl acetate (.x.5) and all of the organic fraction were then combined, dried over sodium sulfate, filtered and the filtrate was concentrated under reduced pressure. The solid that remained was triturated with ethyl acetate to give the title compound which was used without further purification.Yield: 2.97g (62percent of theory)Analysis: 1H NMR (500 MHz, dimethyl sulfoxide-d6) in ppm 4.49 (2H, s), 11.55 (1H, br. s.), 11.70 (1H, br. s.)
	In methanol; at 20℃; for 72h;	Step 14.0 g Semicarbazide hydrochloride, 9.67 mL 2-chloro-1 ,1 ,1 -trimethoxyethane and 40 mL methanol were combined and stirred at ambient temperature for 3 d. After this time additional 3.5 mL 2-chloro-1 ,1 ,1 -trimethoxyethane was added to complete the reaction. The mixture was then concentrated under reduced pressure and the crude product was partitioned between ethyl acetate and 1 N hydrochloric acid. The organic phase separated and it was washed with additional 1 N hydrochloric acid (x2). The combined aqueous extracts were extracted with ethyl acetate (x5) and all of the organic fraction were then combined, dried over sodium sulfate, filtered and the filtrate was concentrated under reduced pressure. The solid that remained was triturated with ethyl acetate to give the title compound which was used without further purification.Yield: 2.97g (62percent of theory)Analysis: 1H NMR (500 MHz, dimethyl sulfoxide-d6) in ppm 4.49 (2 H, s), 1 1.55 (1 H, br. s.), 1 1.70 (1 H, br. s.)
	In methanol; at 20℃; for 144h;	A mixture of semicarbazide hydrochloride (5 g, 44.8 mmol) and 2-chloro- 1, 1, 1- trimethoxyethane (13.29 ml, 99 mmol) in methanol (50 ml) was stirred at room temperature for 3 days at which time the reaction became a homogenous solution. Additional 2-chloro- 1, 1,1- trimethoxyethane (4.3 ml, 32.3 mmol) was added and the reaction was stirred for 3 days longer. The reaction mixture was concentrated and the residue was partitioned in ethyl acetate (500 mL) and IN aqueous HC1 (75 mL). The organic layer was washed with additional IN aqueous HC1 (2 x 75 mL). The combined aqueous layers were back-extracted with additional ethyl acetate (5 x 100 mL). The organic extracts were combined, dried over anhydrous sodium sulfate, filtered, and concentrated to afford the title compound. MS (DCI+) m/z 150.9 (M+NH4)+.

In methanol; at 20℃; for 3h;

Example 325-chloromethyl-2,4-dihydro-l ,2,4-triazol~3-one (74); [0718] Semicarbazide.HCl (5 g, 89 mmol), 2-chloro-l,l,l-trimethoxyethane (12.07 mL, 179 mmol) and methanol (50 mL) were combined and stirred at room temperature for 3 days, with the reaction monitored by 1H NMR. Additional 2-chloro- 1,1,1 -trimethoxyethane (8.77 mL) was added to complete the reaction. Methanol was then removed under vacuum. The resulting residue was extracted with ethyl acetate (500 mL) and washed with IN HCl (2 x 100 mL). The aqueous phase was back extracted with ethyl acetate (5 X 100 mL). The organic layers were then combined, dried over anhydrous sodium sulfate, and solvent was removed under reduced pressure to give 3.1 g of 5-chloromethyl-2,4-dihydro-l,2,4-triazol-3- one (74) as a white powder. 1H NMR (DMSO-d6): delta 11.65 (s, 1H), 11.50 (s, 1H), 4.48 (s, 2H); LCMS (m/z): 133.90 (M+).

Reference： [1]Tetrahedron Letters,2000,vol. 41,p. 8661 - 8664
[2]Patent: US2012/28939,2012,A1 .Location in patent: Page/Page column 27
[3]Patent: WO2011/92128,2011,A1 .Location in patent: Page/Page column 51-52
[4]Patent: WO2014/139328,2014,A1 .Location in patent: Page/Page column 614
[5]Patent: WO2006/133426,2006,A2 .Location in patent: Page/Page column 276

2
[ 112253-70-0 ]
[ 74974-54-2 ]
[ 573681-17-1 ]

Yield	Reaction Conditions	Operation in experiment
	for 0.5h;Heating / reflux;	Reflux a solution of <strong>[112253-70-0]2-amino-4-bromobenzamide</strong> (27 g, 0.13 mol; see Joshi and Chaudhari (1987) Indian J. CHEM., Sect. B, 26B (6) : 602-4) in 2-CHLORO-1, 1, 1-TRIMETHOXYETHANE (50 mL) for 30 minutes, during which time a large precipitate appears. Evaporate the mixture fully and triturate with ether to collect 7-BROMO-2-CHLOROMETHYL-3H-QUINAZOLIN-4-ONE as a white solid

Reference： [1]Patent: WO2004/55003,2004,A1 .Location in patent: Page 121

3
[ 74974-54-2 ]
[ 252742-72-6 ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; toluene;	EXAMPLE 1 3-Chloromethyl-1,2,4-triazolin-5-one A mixture of semicarbzide hydrochloride (5.69 Kg, 51.0 mol), 2-chloro-1,1,1-trimethoxy ethane (94.0 mol) and methanol (54 L) was stirred at room temperature for 4 days. The solvent was then removed under reduced pressure and toluene (25 L) was added. The resulting slurry was cooled to 0° C. and filtered to afford 3-chloromethyl-1,2,4-triazolin-5-one (6.69 Kg, 98percent) as a white solid (mp 197-199° C.); 1H NMR (d6 DMSO) delta=4.43 (2H, s, CH2), 11.48 (1H, s, NH) and 11.64 (1H, s NH); 13C NMR (d6 DMSO) delta=36.9 (ClCH2), 144.6 (CH2C=N) and 156.9 (NHCONH). The difficulty in following the reaction of such water soluble compounds has been overcome using the following HPLC conditions:

Reference： [1]Patent: US2003/187274,2003,A1

4
[ 17672-21-8 ]
[ 74974-54-2 ]
[ 1006601-77-9 ]

Yield	Reaction Conditions	Operation in experiment
66%	In ethanol; for 6h;Heating / reflux;	Step B: A mixture of <strong>[17672-21-8]methyl 2-amino-3-hydroxybenzoate</strong> (3.5 g, 20.70 mmol) and 2-chloro-1,1,1-trimethoxyethane (3.0 mL, 22.06 mmol) in ethanol (30 mL) was stirred under reflux for 6 h. The reaction mixture was cooled to ambient temperature and the solvent volume was reduced under reduced pressure approximately to 2/3 of initial volume. The precipitate formed was filtered, washed with ether (3*10 mL), and dried under vacuum to afford methyl 2-(chloromethyl)benzoxazole-4-carboxylate (3.1 g, 66%) as a yellow solid: 1H NMR (500 MHz, CDCl3) delta 8.05 (dd, J=8.0, 1.0 Hz, 1H), 7.78 (dd, J=9.0, 1.0 Hz 1H), 7.47 (t, J=5.0 Hz, 1H), 4.84 (s, 2H), 4.04 (s, 3H); (APCI+) m/z 226 (M+H).

Reference： [1]Patent: US2008/214601,2008,A1 .Location in patent: Page/Page column 22; 24

5
[ 4426-72-6 ]
[ 74974-54-2 ]
[ 252742-72-6 ]

Yield	Reaction Conditions	Operation in experiment
		5- (chloromethyl)-2,4-dihydro-3H-l,2,4-triazol-3-one (21 mg, 0.156 mmol, 1.03 eq; prepared from semicarbazide and 2-chloro-l,l,l-trimethoxyethane as described by Cameron J. Cowden, Robert D. Wilson, Brian C. Bishop, Ian F. Cottrell, Antony J. Davies and Ulf-eta. Dolling; Tetrahedron Letters, 2000, 41, 8661-8664).

Reference： [1]Patent: WO2009/67233,2009,A1 .Location in patent: Page/Page column 69

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Isomers

Technical Information

? Alkyl Halide Occurrence ? General Reactivity ? Grignard Reaction ? Heat of Combustion ? Hiyama Cross-Coupling Reaction ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Nomenclature of Ethers ? Preparation of Ethers ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Ethers ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling

Historical Records

Related Functional Groups of
[ 74974-54-2 ]

Aliphatic Chain Hydrocarbons

[ 51076-95-0 ]

2-Chloro-1,1,1-triethoxyethane

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[ 97-97-2 ]

2-Chloro-1,1-dimethoxyethane

Similarity: 0.86

Chlorides

[ 51076-95-0 ]

2-Chloro-1,1,1-triethoxyethane

Similarity: 0.91

[ 97-97-2 ]

2-Chloro-1,1-dimethoxyethane

Similarity: 0.86

Ethers

[ 51076-95-0 ]

2-Chloro-1,1,1-triethoxyethane

Similarity: 0.91

[ 97-97-2 ]

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[ CAS No. 74974-54-2 ] {[proInfo.proName]}

Quality Control of [ 74974-54-2 ]

Related Doc. of [ 74974-54-2 ]

Product Details of [ 74974-54-2 ]

Safety of [ 74974-54-2 ]

Application In Synthesis of [ 74974-54-2 ]

[ 74974-54-2 ] Synthesis Path-Upstream 1~3

[ 74974-54-2 ] Synthesis Path-Downstream 1~5

Technical Information

Related Functional Groups of [ 74974-54-2 ]

Aliphatic Chain Hydrocarbons

Chlorides

Ethers

Precautionary Statements-General

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Response

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Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 74974-54-2 ]