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[ CAS No. 20485-43-2 ]

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2D
Chemical Structure| 20485-43-2
Chemical Structure| 20485-43-2
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Product Details of [ 20485-43-2 ]

CAS No. :20485-43-2MDL No. :MFCD01863421
Formula : C5H6N2O2 Boiling Point : 339.4°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :126.11Pubchem ID :557678
Synonyms :

Computed Properties of [ 20485-43-2 ]

TPSA : 55.1 H-Bond Acceptor Count : 3
XLogP3 : -0.1 H-Bond Donor Count : 1
SP3 : 0.20 Rotatable Bond Count : 1

Safety of [ 20485-43-2 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 20485-43-2 ]

  • Upstream synthesis route of [ 20485-43-2 ]
  • Downstream synthetic route of [ 20485-43-2 ]

[ 20485-43-2 ] Synthesis Path-Upstream   1~10

  • 1
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Reference: [1] Journal of the American Chemical Society, 1957, vol. 79, p. 4922,4926
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Reference: [1] Journal of the American Chemical Society, 1957, vol. 79, p. 4922,4926
  • 3
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YieldReaction ConditionsOperation in experiment
100% With dihydrogen peroxide In water at 20℃; for 72 h; First, 1-methylimidazole-2-carboxaldehyde was prepared according to the literature procedure[23]. The synthesis procedure then followed that of Im2COOH (1b) above and the yield was also quantitative after the removal of water under high vacuum (no washing with diethylether/water was necessary). Note: heating causes decarboxylation. Yield: 100percent. Mp=99–101°C. δH (400MHz, D2O): 7.42, 7.39 (2H, s, Im-H) and 4.08ppm (3H, s, NCH3); δC (400MHz, D2O): 158.67, 139.68, 125.83, 118.46, 36.73ppm. IR ν (KBr): 3347(m) 3119(m), 2663(w), 1641(s), 1683(m), 1507(s), 1449(m), 1388(s), 1338(s), 1285(s), 1173(m), 1123(s), 961(m) 910(m), 776(s), 685(s) cm−1. Anal. Calc. for C5H8N2O3 (144.12); C, 41.67; H, 5.59; N, 19.44percent. Found: C, 41.28; H, 5.23; N, 19.12percent.
Reference: [1] South African Journal of Chemistry, 2010, vol. 63, p. 95 - 104
[2] Journal of Inorganic Biochemistry, 2015, vol. 145, p. 11 - 18
[3] South African Journal of Chemistry, 2012, vol. 65, p. 231 - 238
  • 4
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YieldReaction ConditionsOperation in experiment
77%
Stage #1: for 1 h; Heating / reflux
Stage #2: With hydrogenchloride In water at 5 - 50℃;
Dry acetonitrile (600 ML) was added to N-methylimidazole (150 g, 1.8 mol), followed by triethylamine (503 ML, 3.6 mol) in one portion, and the mixture cooled TO-30 °C. Neat ethyl chloroformate (350 mL, 3.6 mol) was added slowly over 15 min. The turbid mixture was then warmed to room temperature and maintained overnight. The solid triethyl ammonium chloride was filtered off, washed with EtOAc, and the filtrate concentrated in vacuo. Dichloromethane (500 ML) was added and the solution was extracted with water (300 mL), the organic phase dried with magnesium sulfate, and concentrated in vacuo. The residue was purified by flash chromatography (SIO2, EtOAc) and recrystallization from ether/heptane (2: 1) to provide 188 g (66percent) of N-METHYLIMIDAZOLE-2-CARBOXY ethyl ester. This N-methylimidazole-2-carboxy ethyl ester (120 g, 0.77 mol) was treated with a solution of sodium hydroxide (37 g, 0.9 mol) in water (60 mL), and the mixture heated at reflux for 1 h. The mixture cooled to 50 °C, acidified to pH 2 with concentrated HC1, cooled further to 5 °C and the precipitate filtered. The solid was washed with ether, diluted into water (70 mL), heated gently under 60 °C, and upon cooling the product crystallizes to give 75 g (77percent) of N-METHYLIMIDAZOLE-2-CARBOXYLIC acid, which was converted into the corresponding aldehyde as described for Intermediate 23.
Reference: [1] Patent: WO2004/58763, 2004, A1, . Location in patent: Page 43
  • 5
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YieldReaction ConditionsOperation in experiment
98%
Stage #1: With sodium hydroxide In water for 1 h; Reflux
Stage #2: With hydrogenchloride In water
A solution of the methylimidazole (3.2 mL, 40.0 mmol) in 30 mL de CH3CN:Et3N (2:1) was cooled to –30 C and quickly added to a previously prepared solution of ethyl chloroformiate (7 mL, 66.0 mmol) in 10 mL of CH3CN. The mixture was stirred for 15h at rt. The solvents were removed under reduced pressure; the crude was re-dissolved in water (20 mL) and extracted with chloroform (3 × 20 mL). The organic fractions were dried and concentrated, and the resulting residue was purified by flash cromatography (aluminum oxide, 90percent MeOH) to give 3.72 g of a crude ester residue which was directly used for the next step. A solution of this residue (1.5 g, 9.74 mmol) in 15 mL of aqueous NaOH (1 M) was refluxed for 1 h. The resulting mixture was acidified to pH 2.0 using HCl 10percent (aprox.15 mL) and lyophilized. The crude was dissolved in MeOH and concentrated underreduced pressure to give 12 as a slighlty pink solid (1.2 g, 98percent).
Reference: [1] Tetrahedron, 2013, vol. 69, # 36, p. 7847 - 7853
  • 6
  • [ 541-41-3 ]
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YieldReaction ConditionsOperation in experiment
82% With triethylamine In acetonitrile Ethy 1-methylimidazole-2-carboxylate
N-methylnimdazole (320 g, 3.9 mol) was combined with 2 L acetonitrile and 1 L triethylamine in a 12 L flask equipped with a mechanical stirrer and the solution cooled to -20° C. Ethyl chloroformate (1000 g, 9.2 mol) was added with stirring, keeping the temperature between -20° C. and -25° C.
The reaction was allowed to slowly warm to room temperature and stir for 36 h.
Precipitated triethylamine hydrochloride was removed by filtration and the solution concentrated in vacuo at 65° C.
The resulting oil was purified by distillation under reduced pressure (2 torr, 102° C.) to provide a white solid (360 g, 82percent yield).
Reference: [1] Patent: US6143901, 2000, A,
  • 7
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Reference: [1] Journal of the American Chemical Society, 2010, vol. 132, # 26, p. 8858 - 8859
[2] Journal of the American Chemical Society, 1992, vol. 114, # 23, p. 8783 - 8794
  • 8
  • [ 616-47-7 ]
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Reference: [1] Journal of the American Chemical Society, 1957, vol. 79, p. 4922,4926
  • 9
  • [ 616-47-7 ]
  • [ 109-72-8 ]
  • [ 41806-40-0 ]
  • [ 20485-43-2 ]
Reference: [1] Journal of the American Chemical Society, 1957, vol. 79, p. 4922,4926
  • 10
  • [ 616-47-7 ]
  • [ 109-72-8 ]
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Reference: [1] Journal of the American Chemical Society, 1957, vol. 79, p. 4922,4926
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