3-Chloroaniline → N-(3-Chlorophenyl)-5-methyl-1H-imidazole-4-carboxamide

HRID 1285224Notes

Reaction equation

HRID 1285224 reaction equation
[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[C:7](Cl)=[O:8].[Cl:10][C:11]1[CH:12]=[C:13]([CH:15]=[CH:16][CH:17]=1)[NH2:14]>N1C=CC=CC=1>[Cl:10][C:11]1[CH:12]=[C:13]([NH:14][C:7]([C:3]2[N:4]=[CH:5][NH:6][C:2]=2[CH3:1])=[O:8])[CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 79323-ChloroanilineHCID 202680235-methyl-1H-imidazole-4-carboxylic acid chloride

Product 1

HCID 13588451N-(3-Chlorophenyl)-5-methyl-1H-imidazole-4-carboxamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Under a dry nitrogen atmosphere a solution of 5-methyl-1H-imidazole-4-carboxylic acid chloride (1.5 g, 0.01 mole) and 3-chloroaniline (1.3 g, 0.01 mole) in 25 ml of pyridine was stirred at ambient temperature for two days. The reaction mixture was then concentrated under reduced pressure, and the residue was slurried with aqueous saturated sodium bicarbonate. The resultant solid was collected by filtration, washed with water, and recrystallized, yielding N-(3-chlorophenyl)-5-methyl-1H-imidazole-4-carboxamide; (0.5 g; mp, 199°-202°).

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. filtrationThe resultant solid was collected by filtration
  3. washwashed with water
  4. customrecrystallized

Sources & evidence

ORD record
ord-efd268cf60b7488aba4340910915ae55
Source dataset
uspto-grants-1986_01
Patent number
US04565875

Reaction notes

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