Toluene → 1-Phenylcarbamoyl-2-methyl-5-nitroimidazole

HRID 2071293Notes

Reaction equation

HRID 2071293 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][C:20]([N+:23]([O-:25])=[O:24])=[CH:21][N:22]=1>O>[C:1]1([NH:7][C:8]([N:19]2[C:20]([N+:23]([O-:25])=[O:24])=[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 127602-Methyl-5-nitroimidazole

Product 1

HCID 214134141-Phenylcarbamoyl-2-methyl-5-nitroimidazoleYield 82.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 11.9 g. (0.1 mol.) of phenylisocyanate in 75 ml. of toluene is added dropwise to the stirred suspension of 15.2 g. (0.12 mol.) of 2-methyl-5-nitroimidazole in 60 ml. of water at 10° to 12° C. When the addition is complete, the mixture is stirred for further 4 hours. The separated product is filtered off, washed and dried. 20.4 g. (82.9%) of 1-phenylcarbamoyl-2-methyl-5-nitroimidazole are obtained; m.p.: 218°-220° C.

Workup

  1. customat 10° to 12° C
  2. additionWhen the addition
  3. filtrationThe separated product is filtered off
  4. washwashed
  5. customdried

Sources & evidence

ORD record
ord-ae37599f2aeb450fac37b23997e99929
Source dataset
uspto-grants-1977_09
Patent number
US04046773

Reaction notes

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