Cyanogen Bromide → 2-Amino-1-(4-chlorobenzyl)-5-trifluoromethylbenzimidazole

HRID 1034210Notes

Reaction equation

HRID 1034210 reaction equation
Cl.[Cl:2][C:3]1[CH:21]=[CH:20][C:6]([CH2:7][NH:8][C:9]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:10]=2[NH2:11])=[CH:5][CH:4]=1.[N:22]#[C:23]Br>CN(C=O)C.C(N(CC)CC)C>[NH2:22][C:23]1[N:8]([CH2:7][C:6]2[CH:20]=[CH:21][C:3]([Cl:2])=[CH:4][CH:5]=2)[C:9]2[CH:15]=[CH:14][C:13]([C:16]([F:17])([F:18])[F:19])=[CH:12][C:10]=2[N:11]=1

Participants

5

Reactant 2

HCID 10476Cyanogen BromideHCID 190237371,2-Benzenediamine, N1-[(4-chlorophenyl)methyl]-4-(trifluoromethyl)-, hydrochloride (1:1)

Product 1

HCID 1277222-Amino-1-(4-chlorobenzyl)-5-trifluoromethylbenzimidazole

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To an ice cooled solution of 2-(4-chlorobenzylamino)-5-trifluoromethylaniline hydrochloride (6.74 g, 20 mmol) in DMF (100 ml) and triethylamine (2.8 ml) was added cyanogen bromide (2.75 g, 26 mmol). The ice bath was removed after two hours and the mixture was stirred overnight at room temperature. The reaction mixture was diluted with water and neutralized with an aqueous solution of sodium carbonate (5%). The product was filtered off and purified with activated charcoal and crystallization from ethanol. Yield 2.93 g (45%).

Workup

  1. customThe ice bath was removed after two hours
  2. additionThe reaction mixture was diluted with water
  3. filtrationThe product was filtered off
  4. custompurified with activated charcoal and crystallization from ethanol

Sources & evidence

ORD record
ord-c4ade3f8a9ae4bbdb21e038f648467f0
Source dataset
uspto-grants-1994_05
Patent number
US05314903

Reaction notes

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