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

HRID 2186079Notes

Reaction equation

HRID 2186079 reaction equation
[CH2:1]([N:5]1[C:9]2[CH:10]=[CH:11][C:12]([NH2:14])=[CH:13][C:8]=2[N:7]=[CH:6]1)[CH:2]([CH3:4])[CH3:3].[Br:15]Br.N.CO.C(Cl)Cl>CC(O)=O>[CH2:1]([N:5]1[C:9]2[CH:10]=[CH:11][C:12]([NH2:14])=[C:13]([Br:15])[C:8]=2[N:7]=[CH:6]1)[CH:2]([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 24408BromineHCID 18379906HCID 18379906, compoundHCID 21226129Dichloromethane methanol

Product 1

HCID 183798691-Isobutyl-4-bromo-5-aminobenzimidazoleYield 35%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of 1-isobutyl-5-aminobenzimidazole (2.4 g, 13 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-e6f7927a0a664b49aec5533f1223cffb
Source dataset
uspto-grants-2002_06
Patent number
US06403626B1

Reaction notes

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