1H-Benzimidazole-6-carbonitrile → 5-(Trifluoromethoxy)-1H-benzimidazole

HRID 1363125Notes

Reaction equation

HRID 1363125 reaction equation
[N+:1]([C:4]1[CH:10]=[C:9]([O:11][C:12]([F:15])([F:14])[F:13])[CH:8]=[CH:7][C:5]=1[NH2:6])([O-])=O.N1C2C=CC(C#N)=CC=2N[CH:17]=1.NC1C=CC(C#N)=CC=1[N+]([O-])=O>>[F:13][C:12]([F:15])([F:14])[O:11][C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[CH:17][NH:1][C:4]=2[CH:10]=1

Participants

4

Reactant 3

HCID 2239061H-Benzimidazole-6-carbonitrileHCID 5959014-Amino-3-nitrobenzonitrileHCID 27757722-Nitro-4-(trifluoromethoxy)aniline

Product 1

HCID 180055005-(Trifluoromethoxy)-1H-benzimidazole

Procedure

6-(trifluoromethoxy)-1H-benzo[d]imidazole (4) was prepared in two steps from 2-nitro-4-(trifluoromethoxy)aniline (5) using procedures identical to those used to make 3H-benzo[d]imidazole-5-carbonitrile (3) from 4-amino-3-nitrobenzonitrile (1, examples 1, 2).

Sources & evidence

ORD record
ord-9fbf3ff7c3fc43b0bbf745062f5ebbf4
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

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