Toluene → 2-Methyl-N-phenyl-1H-imidazole-1-carboxamide

HRID 2071292Notes

Reaction equation

HRID 2071292 reaction equation
[C:1]1([N:7]=[C:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C)C=CC=CC=1.[CH3:17][C:18]1[NH:19][CH:20]=[CH:21][N:22]=1>O>[C:1]1([NH:7][C:8]([N:19]2[CH:20]=[CH:21][N:22]=[C:18]2[CH3:17])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 7672Phenyl isocyanateHCID 127492-Methylimidazole

Product 1

HCID 123944202-Methyl-N-phenyl-1H-imidazole-1-carboxamideYield 69.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 11.9 g. (0.1 mol.) of phenylisocyanate in 120 ml. of toluene is added to the stirred solution of 8.61 g. (0.105 mol.) of 2-methyl-imidazole in 60 ml. of water under cooling at a temperature of 10 to 12° C. The reaction mixture is stirred at room temperature for one hour, thereafter the separated product is filtered off, washed and dried. 14.0 g. (69.6%) of 1-phenylcarbamoyl-2-methyl-imidazole are obtained; m.p.: 205°-207° C.

Workup

  1. filtrationthe separated product is filtered off
  2. washwashed
  3. customdried

Sources & evidence

ORD record
ord-4f4711f3094442c6bd7ec1be89b8fefc
Source dataset
uspto-grants-1977_09
Patent number
US04046773

Reaction notes

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