Methyl iodide → (4-Bromophenyl)(5-nitrobenzimidazol-2-yl)amine

HRID 1915664

Reaction equation

HRID 1915664 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([NH2:11])[C:7]([NH2:10])=[CH:8][CH:9]=1)([O-:3])=[O:2].[Br:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]=[C:20]=S)=[CH:15][CH:14]=1.IC>CO>[Br:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20]2[NH:11][C:6]3[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:9]=[CH:8][C:7]=3[N:10]=2)=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 161334-Bromophenyl isothiocyanateHCID 51117914-Nitro-1,2-phenylenediamine

Product 1

HCID 22041081(4-Bromophenyl)(5-nitrobenzimidazol-2-yl)amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A solution of the 4-nitrobenzene-1,2-diamine in methanol was treated with 4-bromo phenyl isothiocyanate (1 eq) and stirred at 60° C. for 2 hours. The reaction mixture was cooled down to room temperature and iodomethane (1 eq) was added and stirred overnight at 60° C. The reaction was concentrated and purified on silica gel to yield (4-bromophenyl)(5-nitrobenzimidazol-2-yl)amine. The product was taken in methanol and hydrogenated with catalytic amount of 10% Pd/C to give ((5-aminobenzimidazol-2-yl)(4-bromophenylamine). MS: MH+=302.

Workup

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. stirringstirred overnight at 60° C
  3. concentrationThe reaction was concentrated
  4. custompurified on silica gel

Sources & evidence

ORD record
ord-c4ba23231a784babb90d09e3a6a5a6aa
Source dataset
uspto-grants-2013_12
Patent number
US08614330B2

Linked notes

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