3,4-Difluoroaniline → HCID 11566903, compound

HRID 1176664Notes

Reaction equation

HRID 1176664 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.[F:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][C:19]=1[F:20])[CH2:15]Br.[F:21][C:22]1[CH:23]=[C:24]([CH:26]=[CH:27][C:28]=1[F:29])[NH2:25]>CO.CCOCC>[F:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][C:19]=1[F:20])[CH2:15][N:6]1[C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=[C:2]1[NH:25][C:24]1[CH:26]=[CH:27][C:28]([F:29])=[C:22]([F:21])[CH:23]=1

Participants

5

Reactant 3

HCID 774693,4-DifluoroanilineHCID 785722-ChlorobenzimidazoleHCID 5814364-(Bromomethyl)-1,2-difluorobenzene

Product 1

HCID 11566903HCID 11566903, compound

Reagents, catalysts & solvents 1

HCID 21864698Diethyl ether methanolSolvent

Procedure

The title compound was prepared by Procedure B in two steps from 2-chloro-benzimidazole, 3,4-difluorobenzyl bromide and 3,4-difluoroaniline. The product was isolated by filtration and recrystallization (MeOH/Et2O) to give the title compound as its hydrochloride salt (white solid, mp 236-238° C.). MS(ES+) m/z 372 ([M+1]+, 100). 1NMR (DMSO-d6) δ 5.61 (s, 2H), 7.19-7.30 (m, 3H), 7.36-7.61 (m, 6H), 7.83-7.91 (m, 1H), 11.0 (br s, 1H).

Sources & evidence

ORD record
ord-71cfb61a15a54ea48757649904051042
Source dataset
uspto-grants-2010_11
Patent number
US07842817B2

Reaction notes

Loading…