Water → 5-Chloro-6-(trifluoromethyl)-1H-benzimidazol-2-amine

HRID 639746Notes

Reaction equation

HRID 639746 reaction equation
Br[C:2]#[N:3].O.[Cl:5][C:6]1[C:11]([C:12]([F:15])([F:14])[F:13])=[C:10](N)[C:9]([NH2:17])=[CH:8][CH:7]=1.C(#[N:20])C>CO>[Cl:5][C:6]1[C:11]([C:12]([F:15])([F:14])[F:13])=[CH:10][C:9]2[NH:17][C:2]([NH2:3])=[N:20][C:8]=2[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6342AcetonitrileHCID 10476Cyanogen BromideHCID 68704666HCID 68704666, compound

Product 1

HCID 587944535-Chloro-6-(trifluoromethyl)-1H-benzimidazol-2-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

318 mg (3 mmol) BrCN are dissolved in 0.6 ml acetonitrile and treated with 6 ml water. To this solution, 575 mg (2.73 mmol) 5-chloro-6-trifluoromethyl-benzene-1,2-diamine, dissolved in 6 ml methanol, are added dropwise within 30 min. After 2 hrs of stirring at room temperature, the reaction mixture is concentrated and the water solution extracted 2× with ethyl acetate. The combined organic phases where re-extracted 1× with water. The combined water phases where made alkaline (pH=8) with saturated NaHCO3-solution and extracted 2× with ethyl acetate. The combined organic phases where dried, filtered and evaporated.

Workup

  1. additionare added dropwise within 30 min
  2. concentrationthe reaction mixture is concentrated
  3. extractionthe water solution extracted 2× with ethyl acetate
  4. extractionThe combined organic phases where re-extracted 1× with water
  5. extractionextracted 2× with ethyl acetate
  6. customThe combined organic phases where dried
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-9bf42ed55def4cb28e00bfe0b1e343b5
Source dataset
uspto-grants-2010_04
Patent number
US07691886B2

Reaction notes

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