Cyanogen Bromide → Methyl 2-amino-1H-benzimidazole-6-carboxylate

HRID 49929Notes

Reaction equation

HRID 49929 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[NH2:12])[C:5]([O:7][CH3:8])=[O:6].[N:13]#[C:14]Br>O.C(#N)C>[NH2:13][C:14]1[NH:1][C:2]2[CH:3]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[CH:9]=[CH:10][C:11]=2[N:12]=1

Participants

5

Reactant 2

HCID 10476Cyanogen BromideHCID 1355243,5-Diamino-2-methylbenzoic acid

Product 1

HCID 17834337Methyl 2-amino-1H-benzimidazole-6-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

300 mg (1.8 mmol) of methyl 3,4-diaminobenzoate was stirred in 5 ml of water. 0.5 ml of a solution of 5 M of cyanogen bromide in acetonitrile was added to the obtained mixture, and they were stirred at room temperature for 20 minutes. The mixture was filtered. Aqueous ammonia was added to the filtrate. After the treatment with ethyl acetate as the extracting solvent by an ordinary method, the title compound was obtained.

Workup

  1. filtrationThe mixture was filtered
  2. additionAqueous ammonia was added to the filtrate

Sources & evidence

ORD record
ord-19be3b710f6043ff9d1a1cad7a13f50d
Source dataset
uspto-grants-2004_03
Patent number
US06710056B2

Reaction notes

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