Hydrochloric Acid → 4-bromo-2-methyl-1-(2-methyl-3-(trifluoromethyl)benzyl)-1H-benzo[d]imidazol-6-amine

HRID 1622445Notes

Reaction equation

[Br:1][C:2]1[C:10]2[N:9]=[C:8]([CH3:11])[N:7]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[C:14]=3[CH3:23])[C:6]=2[CH:5]=[C:4]([N+:24]([O-])=O)[CH:3]=1.Cl.Cl[Sn]Cl>CO>[Br:1][C:2]1[C:10]2[N:9]=[C:8]([CH3:11])[N:7]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:21])([F:20])[F:22])[C:14]=3[CH3:23])[C:6]=2[CH:5]=[C:4]([NH2:24])[CH:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 4-bromo-2-methyl-1-(2-methyl-3-(trifluoromethyl)benzyl)-6-nitro-1H-benzo[d]imidazole (55 g, 129 mmol) in methanol (600 mL) was added conc. HCl (20 mL), SnCl2 (174 g, 771 mmol) and the mixture was stirred at 70° C. for 2 h. Then the solvent was removed in vacuo, and the residue was diluted with 1N Na2CO3 solution (1.5 L) and extracted with DCM (200 mL×5). The combined organic layers were washed with brine, dried over sodium sulphate and evaporated to give the crude product (45 g, 88%) as a white solid; LC/MS: MS (ES+) m/e 398 [M+H]+; 1H NMR (300 MHz, DMSO-d6) δ ppm 2.37 (s, 3H), 2.52 (s, 3H), 5.06 (s, 2H), 5.40 (s, 2H), 6.35 (d, J=1.8 Hz, 1H), 6.37 (d, J=7.8 Hz, 1H), 6.74 (d, J=1.8 Hz, 1H), 7.26 (t, J=7.8 Hz, 1H), 7.60 (d, J=7.8 Hz, 1H).

Workup

customThen the solvent was removed in vacuo
additionthe residue was diluted with 1N Na2CO3 solution (1.5 L)
extractionextracted with DCM (200 mL×5)
washThe combined organic layers were washed with brine
dry with materialdried over sodium sulphate
customevaporated

Sources & evidence

ORD record: ord-8631d58ca43b420fb9f111b495095e5c
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778937B2

Reaction notes

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