Potassium Carbonate → HCID 13423628, compound

HRID 1788897Notes

Reaction equation

HRID 1788897 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]([O:8][CH2:9][CH3:10])=[O:7].[N+:11]([C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH2:16]Cl)([O-:13])=[O:12].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[N+:11]([C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH2:16][N:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]([O:8][CH2:9][CH3:10])=[O:7])([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 119212-Nitrobenzyl chlorideHCID 549404ethyl 1H-imidazole-2-carboxylate

Product 1

HCID 13423628HCID 13423628, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 14 g (0.1 mol) of ethyl imidazol-2-carboxylate, 18.9 g (0.11 mol) of o-nitrobenzyl chloride, 13.8 g (0.1 mol) of anhydrous potassium carbonate and 100 ml of dimethylformamide was heated at 100° C. for 2 hours while stirring. Then, the solvent was substantially distilled off in vacuo, the residue was mixed with 100 ml of water and extracted with ethyl acetate. The organic phase was washed twice with water, dried over anhydrous sodium sulfate and concentrated by evaporation. The crystalline residue was suspended in ether, and the suspension was suction-filtered. 23.5 g (85.4% of theory) of ethyl 1-(2-nitrobenzyl)-imidazole-2-carboxylate, m.p. 107°-111° C., were obtained.

Workup

  1. distillationThen, the solvent was substantially distilled off in vacuo
  2. additionthe residue was mixed with 100 ml of water
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed twice with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated by evaporation
  7. filtrationthe suspension was suction-filtered

Sources & evidence

ORD record
ord-01fa6ac283af4ba48f163633f0be11dd
Source dataset
uspto-grants-1987_08
Patent number
US04686219

Reaction notes

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