Cyanogen Bromide → 4-Chloro-1H-benzimidazol-2-amine

HRID 415128Notes

Reaction equation

HRID 415128 reaction equation
[N:1]#[C:2]Br.[Cl:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH2:11])[C:6]=1[NH2:12]>C(#N)C.O>[Cl:4][C:5]1[C:6]2[N:12]=[C:2]([NH2:1])[NH:11][C:7]=2[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 10476Cyanogen BromideHCID 3462489(2-Amino-3-chlorophenyl)amine

Product 1

HCID 190177674-Chloro-1H-benzimidazol-2-amine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Cyanogen bromide was added to a solution of 3-chlorobenzene-1,2-diamine (0.81 g, 0.570 mmol) in acetonitrile (10 mL) and water (2 ml) at 0° C. The reaction mixture was allowed to warm to room temperature and stirred for 14 hours. The reaction was quenched with saturated aqueous sodium hydrogen carbonate (50 ml) and shaken. The resulting solid was filtered off, was washed with water and dried at reduced pressure to 0.49 g of 4-chloro-1H-benzo[d]imidazol-2-amine (yield, 49%). MS (EI): 168 (MH+).

Workup

  1. customThe reaction was quenched with saturated aqueous sodium hydrogen carbonate (50 ml)
  2. stirringshaken
  3. filtrationThe resulting solid was filtered off
  4. washwas washed with water
  5. dry with materialdried at reduced pressure to 0.49 g of 4-chloro-1H-benzo[d]imidazol-2-amine (yield, 49%)

Sources & evidence

ORD record
ord-8c8c9d41dd184f2db2a6549e7946e81b
Source dataset
uspto-grants-2012_01
Patent number
US08088767B2

Reaction notes

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