Ammonia → 1-Isopropyl-4-bromo-5-aminobenzimidazole

HRID 429557Notes

Reaction equation

HRID 429557 reaction equation
[CH:1]([N:4]1[C:8]2[CH:9]=[CH:10][C:11]([NH2:13])=[CH:12][C:7]=2[N:6]=[CH:5]1)([CH3:3])[CH3:2].[Br:14]Br.N.CO.C(Cl)Cl>CC(O)=O>[CH:1]([N:4]1[C:8]2[CH:9]=[CH:10][C:11]([NH2:13])=[C:12]([Br:14])[C:7]=2[N:6]=[CH:5]1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 24408BromineHCID 162441621-Isopropyl-1H-benzoimidazol-5-ylamineHCID 21226129Dichloromethane methanol

Product 1

HCID 183798291-Isopropyl-4-bromo-5-aminobenzimidazoleYield 35%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of 1-isopropyl-5-aminobenzimidazole (2.4 g, 14 mmol) in 20 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/CH2Cl2) to provide 1.2 g (4.5 mmol, 35%) 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-f7bcc4ff73f244698d787ca26ba5ffa3
Source dataset
uspto-grants-2001_11
Patent number
US06316637B1

Reaction notes

Loading…