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[ CAS No. 1871-89-2 ] {[proInfo.proName]}

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Chemical Structure| 1871-89-2
Chemical Structure| 1871-89-2
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Product Details of [ 1871-89-2 ]

CAS No. :1871-89-2 MDL No. :MFCD00020559
Formula : C6H12N2O4 Boiling Point : -
Linear Structure Formula :- InChI Key :FPQJEXTVQZHURJ-UHFFFAOYSA-N
M.W : 176.17 Pubchem ID :74638
Synonyms :

Safety of [ 1871-89-2 ]

Signal Word:Danger Class:9
Precautionary Statements:P260-P264-P273-P301+P312-P305+P351+P338-P314 UN#:3077
Hazard Statements:H302-H319-H372-H410 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 1871-89-2 ]

* 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.

  • Downstream synthetic route of [ 1871-89-2 ]

[ 1871-89-2 ] Synthesis Path-Downstream   1~20

  • 1
  • [ 1871-89-2 ]
  • [ 16813-43-7 ]
  • 2
  • [ 1871-89-2 ]
  • [ 98485-17-7 ]
YieldReaction ConditionsOperation in experiment
85% With dinitrogen pentoxide; In carbon dioxide; at 0 - 5℃; under 45004.5 - 60006 Torr; for 0.5h;liquid CO2; General procedure: General nitration procedure.12-14 A steel autoclave (25 cm3) equippedwith sapphire windows containing urethane 1c or amide 3 or 5 (10.0 mmol)was filled with liquid CO2 to 60 bar pressure and cooled to 0 C. ThenN2O5 (2.4 g, 22.0 mmol) solution in liquid CO2 (~ 4 g) cooled to 0-5 Cwas gradually pressed out from an auxiliary high-pressure cell by a freshCO2 flow (2 g min-1) to the reaction autoclave. During the addition, thepressure in the latter raised up to 80 bar. The reaction mixture was stirredat 0-5 C for the time specified in Table 1. Then, CO2 was removed bydecompression and the residue was poured onto ice water (50 ml). Theresulted suspension was extracted with EtOAc (4 × 20 ml), the combinedorganic extracts were washed successively with saturated aqueous NaHCO3(2 × 20 ml) and water (25 ml) and dried over anhydrous Na2SO4. Thesolvent was removed under reduced pressure to afford corresponding nitrocompounds 2, 4 (see Table 1). Compounds 2a,b and 7 were synthesizedby similar procedures using 1.2 g (11.0 mmol) or 6.0 g (55 mmol) ofN2O5, respectively.
  • 3
  • [ 1871-89-2 ]
  • [ 62209-60-3 ]
YieldReaction ConditionsOperation in experiment
90% With dinitrogen pentoxide; In carbon dioxide; at 0 - 5℃; under 45004.5 - 60006 Torr; for 2.0h;liquid CO2; General procedure: General nitration procedure.12-14 A steel autoclave (25 cm3) equippedwith sapphire windows containing urethane 1c or amide 3 or 5 (10.0 mmol)was filled with liquid CO2 to 60 bar pressure and cooled to 0 C. ThenN2O5 (2.4 g, 22.0 mmol) solution in liquid CO2 (~ 4 g) cooled to 0-5 Cwas gradually pressed out from an auxiliary high-pressure cell by a freshCO2 flow (2 g min-1) to the reaction autoclave. During the addition, thepressure in the latter raised up to 80 bar. The reaction mixture was stirredat 0-5 C for the time specified in Table 1. Then, CO2 was removed bydecompression and the residue was poured onto ice water (50 ml). Theresulted suspension was extracted with EtOAc (4 × 20 ml), the combinedorganic extracts were washed successively with saturated aqueous NaHCO3(2 × 20 ml) and water (25 ml) and dried over anhydrous Na2SO4. Thesolvent was removed under reduced pressure to afford corresponding nitrocompounds 2, 4 (see Table 1). Compounds 2a,b and 7 were synthesizedby similar procedures using 1.2 g (11.0 mmol) or 6.0 g (55 mmol) ofN2O5, respectively.
  • 5
  • [ 141-43-5 ]
  • [ 95-92-1 ]
  • [ 1871-89-2 ]
YieldReaction ConditionsOperation in experiment
94% In ethanol; at 20℃; for 24.0h; General procedure: Method A: Diethyl oxalate (0.5 mmol) was added dropwise to a stirred solution of the appropriate amino alcohol 1 (1 mmol) in toluene or ethanol (4 ml). The mixture was stirred at rt for 24 h. If a solid appears was filtered under reduced pressure and analyzed; the filtrate liquid was concentrated to dryness and analyzed by 1H NMR. When not precipitated, the crude reaction mixture was concentrated to dryness and analyzed by 1H NMR. To obtain analytical information the products were purified by column chromatography.
87% In ethylene glycol; at 79 - 80℃; for 3.0h;Conversion of starting material; N,N'-bis (2-hydroxyethyl) oxamide Starting Materials Diethyl oxalate 0.25 mol Monoethanolamine 0.5 mol Ethylene Glycol 250 g. Operating Conditions Pressure Atmospheric Temperature/time regime 79-80 C./3 h. Reaction Progress Monitored by TLC using Merck's silica gel plates and benzene- dimethylformamide (25:4). Work-up The reaction mass was allowed to cool to room temperature, refrigerated (0 C.) and stirred for five minutes before filtration. The filter cake was drained, dried at 70-80 C. overnight, dispersed in ethanol (3 parts ethanol to 1 part solid), the dispersion heated to boiling, cooled and filtered. The filter cake was washed with cold ethanol, drained and dried overnight at 60-80 C. 38.2 g. of white crystals (m.p. 169.9-170.3 C.) were obtained (literature m.p. 166-169 C.) Yield 87%
83% In hexan-1-ol; at 20 - 100℃; for 3.0h; Example 3 Preparation of N,N'-bis(2-hydroxyethyl)oxamide A solution of 17.2 g of ethanolamine dissolved in 20 ml of 1-hexanol is added dropwise to a suspension of 20 g of ethyl oxalate in 100 ml of 1-hexanol. The reaction mixture is then refluxed (100 C.) for 2 hours, and the mixture is then left at room temperature for 1 hour. The precipitate obtained is then filtered off and is recrystallized from a minimum amount of boiling ethanol. 20 g of a white powder are thus obtained (yield: 83%). The 1H and 13C NMR spectra are those of N,N'-bis(2-hydroxy-ethyl)oxamide. An elemental analysis gave:
  • 6
  • [ 1871-89-2 ]
  • [ 496-72-0 ]
  • 5-methyl-1(3)<i>H</i>-benzimidazole-2-carboxylic acid-(2-hydroxy-ethylamide) [ No CAS ]
  • 7
  • [ 1871-89-2 ]
  • [ 95-54-5 ]
  • [ 14484-06-1 ]
  • 8
  • [ 1871-89-2 ]
  • [ 2937-50-0 ]
  • <i>N</i>,<i>N</i>'-bis-(2-allyloxycarbonyloxy-ethyl)-oxalamide [ No CAS ]
  • 9
  • [ 120-86-5 ]
  • [ 1871-89-2 ]
  • 10
  • [ 553-90-2 ]
  • [ 141-43-5 ]
  • [ 1871-89-2 ]
YieldReaction ConditionsOperation in experiment
68% In methanol; at 18℃; for 2.16667h;Inert atmosphere; To a solution of dimethyloxalate (119 g, 1 mol, 1 equi.) in 840 mL MeOH at 18 C. and under N2 flow was added Reagent 06 (2-aminoethanol, 130 g, 2.1 mol, 2.1 equi.) over 90 minutes via a dropping addition funnel. After addition, stirring is continued for 40 min at 18 C. The crude mixture contained a white precipitate which was filtered off and washed three times with 200 mL MeOH. The white solid was dried in a dry oven at 70 C., prior to recrystallization in 2 L refluxing MeOH and further filtration. The collected white solid was recrystallized in 500 mL refluxing MeOH and further filtered off. The white solid was dried in a dry oven at 70 C. Yield: 68%
  • 12
  • [ 471-46-5 ]
  • [ 141-43-5 ]
  • [ 1871-89-2 ]
  • 13
  • [ 816-27-3 ]
  • [ 141-43-5 ]
  • [ 1871-89-2 ]
  • 14
  • [ 141-43-5 ]
  • [ 148705-17-3 ]
  • [ 1871-89-2 ]
YieldReaction ConditionsOperation in experiment
...(4-tert.-butyl-3-hydroxy-2,6-dimethylbenzyl)isocyanurate, dioctadecyl(3,5-di-tert.-butyl-4-hydroxybenzyl)-phosphonate, the calcium salt of monoethyl(3,5-di-tert.-butyl-4-hydroxybenzyl)-phosphonate and tris-(3,5-dicyclohexyl-4-hydroxybenzyl)isocyanurate; 1.6. ... thio-diethylene glycol, pentaerythritol, tris-(hydroxyethyl)isocyanurate and N,N'-bis-(hydroxyethyl)-oxamide; octadecanol, 1,6-hexanediol, neopentylglycol, ...
  • 17
  • [ 95-92-1 ]
  • [ 1871-89-2 ]
YieldReaction ConditionsOperation in experiment
91% In ethanolamine; EXAMPLE 5 Preparation of N,N'-bis-(2-hydroxyethyl)-oxalyldiamide (5) 1.46 g diethyloxalate (10 mmol) were slowly added drop by drop in 30 minutes to 1.34 g ethanolamine (22 mmol) at 0 C. under stirring. The obtained mixture was maintained at 0 C. for 1 hour and then at room temperature for 5 hours. The raw product thus obtained was directly crystallized from 50 ml 80% ethanol, the crystallized product was separated by filtration, washed three times with 10 ml cool ethanol and then dried under high vacuum. The reaction yield was about 91%. The physical-chemical characteristics of the N,N'-bis-(2-hydroxyethyl)-oxalyldiamide are the following:
91% In ethanolamine; Example 5 preparation of N,N'-bis(2-hydroxyethyl)-oxalyldiamide (5) 1.46 g diethyloxalate (10 mmol) were slowly added drop by drop in 30 minutes to 1.34 g ethanolamine (22 mmol) at 0 C under stirring. The obtained mixture was maintained at 0 C for 1 hour and then at room temperature for 5 hours. The raw product thus obtained was directly crystallized from 50 ml 80% ethanol, the crystallized product was separated by filtration, washed three times with 10 ml cool ethanol and then dried under high vacuum. The reaction yield was about 91 %. The physical-chemical characteristics of the N,N'-bis (2-hydroxyethyl)-oxalyldiamide are the following:
  • 18
  • [ 40227-15-4 ]
  • [ 141-43-5 ]
  • [ 1871-89-2 ]
YieldReaction ConditionsOperation in experiment
93% In methanol; EXAMPLE 6 Preparation of N,N'-bis-(2-hydroxyethyl)oxamide A suspension of N,N'-diacetyloxamide (10 g, 0.058 mol) in anhydrous methyl alcohol (50 ml) is charged into a four-necked flask equipped with a reflux condenser, an inlet tube for nitrogen, a dropping funnel, a thermometer, and a magnetic stirrer. A solution of monoethanolamine (8.2 g, 0.134 mol) in anhydrous methyl alcohol (20 ml) is gradually dripped in at 25 C. The reaction is exothermic and the temperature rises up to 60 C. The reaction is allowed to proceed at this temperature for 2 hours, then the reaction mixture is cooled and the precipitate is recovered by filtration. The compound of the title is thus obtained (9.5 g, 0.054 mol, 93% yield) with m.p. 166-69 C. Elemental analysis: Calculated for C6 H12 N2 O4; C 40.91%; H 6.82%; N 15.90%; Calculated for C C 40.91%; H 6.82%; N 15.90%. Found: C 41.0%; H 6.9%; N 15.9%.
  • 19
  • [ 79-37-8 ]
  • [ 1871-89-2 ]
  • [ 16373-06-1 ]
  • 3,3-bis(3,5-di-tert-butyl-4-hydroxyphenyl) butanoic acid, N,N'-bis(2-hydroxyethyl) oxamide diester [ No CAS ]
YieldReaction ConditionsOperation in experiment
In 1,2-dimethoxyethane; EXAMPLE 1 3,3-Bis(3,5-di-tert-butyl-4-hydroxyphenyl) butanoic acid, N,N'-bis(2-hydroxyethyl) oxamide diester 3,3-Bis(3,5-di-tert-butyl-4-hydroxyphenyl) butanoic acid (14.3 g) and oxalyl chloride (25 ml) were combined and reacted at room temperature for 2 hr. Excess oxalyl chloride was removed under vacuum. The residue was dissolved in 90 ml dimethoxyethane and combined with N,N'-bis(2-hydroxyethyl) oxamide (2.41 g). The mixture was refluxed 4 hr. then stirred overnight at room temperature. Solvent was removed under vacuum. The residue was recrystallized from ethanol/water to give 9.1 g of the desired product as a white solid, mp 173-175 C. Cal for: C70 H104 N2 O10: C, 74.17; H, 9.25; N, 2.47. Found: C, 73.95; H, 9.02; N, 2.33.
  • 20
  • [ 52462-29-0 ]
  • [ 1871-89-2 ]
  • [Ru2(p-cymene)2(μ4-bis(2-hydroxyethyl)oxamidato)Cl2] [ No CAS ]
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