4-Chloro-3-(trifluoromethyl)aniline → HCID 11620357, compound

HRID 1176668Notes

Reaction equation

HRID 1176668 reaction equation
Cl[C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[Cl:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16]Br)=[CH:14][C:13]=1[C:20]([F:23])([F:22])[F:21].[Cl:24][C:25]1[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][C:26]=1[C:32]([F:35])([F:34])[F:33]>>[Cl:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16][N:6]2[C:5]3[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=3[N:3]=[C:2]2[NH:29][C:28]2[CH:30]=[CH:31][C:25]([Cl:24])=[C:26]([C:32]([F:35])([F:33])[F:34])[CH:27]=2)=[CH:14][C:13]=1[C:20]([F:23])([F:22])[F:21]

Participants

4

Reactant 3

HCID 675744-Chloro-3-(trifluoromethyl)anilineHCID 785722-ChlorobenzimidazoleHCID 27781144-Chloro-3-(trifluoromethyl)benzyl bromide

Product 1

HCID 11620357HCID 11620357, compound

Procedure

The title compound was prepared by Procedure B in two steps from 2-chloro-benzimidazole, 4-chloro-3-trifluoromethylbenzyl bromide and 4-chloro-3-trifluoromethylaniline. The product was isolated by preparative LCMS to give the title compound as the free base (off-white solid, mp 88-92° C.). MS(ES+) m/z 504 (M+, 100). 1NMR (DMSO-d6) δ 5.60 (s, 2H), 7.02-7.15 (m, 2H), 7.25-7.32 (m, 2H), 7.45-7.52 (m, 1H), 7.63-7.70 (m, 2H), 7.81 (s, 1H), 8.23-8.40 (m, 2H), 9.62 (br s, 1H).

Workup

  1. customThe product was isolated by preparative LCMS

Sources & evidence

ORD record
ord-0cbf4b7cf22a4318919bc6febc3eac1a
Source dataset
uspto-grants-2010_11
Patent number
US07842817B2

Reaction notes

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