Ammonia → 3-Cyclohexylmethyl-4-bromo-5-aminobenzimidazole

HRID 2299136Notes

Reaction equation

HRID 2299136 reaction equation
[CH:1]1([CH2:7][N:8]2[C:12]3[CH:13]=[C:14]([NH2:17])[CH:15]=[CH:16][C:11]=3[N:10]=[CH:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:18]Br.N.CO.C(Cl)(Cl)Cl>CC(O)=O>[CH:1]1([CH2:7][N:8]2[C:12]3[C:13]([Br:18])=[C:14]([NH2:17])[CH:15]=[CH:16][C:11]=3[N:10]=[CH:9]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 24408BromineHCID 183798263-Cyclohexylmethyl-5-aminobenzimidazoleHCID 21584188Chloroform methanol

Product 1

HCID 183798273-Cyclohexylmethyl-4-bromo-5-aminobenzimidazoleYield 48%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of 3-cyclohexylmethyl-5-aminobenzimidazole (2.0 g, 8.7 mmol) in 40 ml of AcOH was added solution of Br2 in AcOH until it produces a precipitation. The reaction mixture was concentrated in vacuo to provide a brown solid which was subjected to column chromatography (5% NH3 sat'd MeOH/CHCl3) to provide 1.2 g (3.8 mmol, 48%) of the product.

Workup

  1. customproduces
  2. customa precipitation
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customto provide a brown solid which

Sources & evidence

ORD record
ord-265df3b086104a628baec8e06f80e2d0
Source dataset
uspto-grants-2002_12
Patent number
US06495583B1

Reaction notes

Loading…