2-Nitroaniline → 2-(3-methylphenyl)benzimidazole

HRID 377239Notes

Reaction equation

HRID 377239 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-])=O.C(N(CC)C1C=CC=CC=1)C.[CH3:22][C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=1)[C:26](Cl)=O>C1(C)C=CC=CC=1>[CH3:22][C:23]1[CH:24]=[C:25]([C:26]2[NH:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[N:8]=2)[CH:29]=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 69462-NitroanilineHCID 7061N,N-DiethylanilineHCID 743753-Methylbenzoyl chloride

Product 1

HCID 28794762-(3-methylphenyl)benzimidazole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

The intermediate 2-(3-methylphenyl)-benzimidazole was prepared by first mixing reacting 1-amino-2-nitrobenzene (8.50 g, 61.54 mmol) with toluene (180 ml) and heating to 100° C. To this mixture was then added 20 ml of N,N-diethylaniline and the reaction vessel was placed under a nitrogen atmosphere. To this solution was then added 3-methylbenzoyl chloride (24 ml, 132 mmol) and this mixture was then stirred overnight.

Workup

  1. additionby first mixing

Sources & evidence

ORD record
ord-ec6085c629304c91bd3944d3f2eb9e24
Source dataset
uspto-grants-2000_02
Patent number
US06025379

Reaction notes

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