Cyanogen Bromide → 1-Methyl-5-nitro-1H-benzimidazol-2-amine

HRID 1391546Notes

Reaction equation

HRID 1391546 reaction equation
[CH3:1][NH:2][C:3]1[C:4]([NH2:12])=[CH:5][C:6]([N+:9]([O-:11])=[O:10])=[CH:7][CH:8]=1.[N:13]#[C:14]Br>CO>[CH3:1][N:2]1[C:3]2[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=2[N:12]=[C:14]1[NH2:13]

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 34200251-N-methyl-4-nitrobenzene-1,2-diamine

Product 1

HCID 450786361-Methyl-5-nitro-1H-benzimidazol-2-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N1-methyl-4-nitro-benzene-1,2-diamine (200 mg, 1.20 mmol) in methanol (12 ml) was added cyanogen bromide (190.1 mg, 1.79 mmol). After stirring at room temperature for 16 h, the methanol was removed in vacuo and the resulting solid was stirred with diethyl ether (40 ml) for 5 minutes. The resulting hydrobromide salt of the title compound was filtered and air-dried.

Workup

  1. customthe methanol was removed in vacuo
  2. stirringthe resulting solid was stirred with diethyl ether (40 ml) for 5 minutes
  3. filtrationThe resulting hydrobromide salt of the title compound was filtered
  4. customair-dried

Sources & evidence

ORD record
ord-a44532fd00534422a86455a70c8c0659
Source dataset
uspto-grants-2008_03
Patent number
US07338959B2

Reaction notes

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