2-Bromopropane → 1H-Benzimidazole,2-chloro-1-(1-methylethyl)-(9CI)

HRID 1703182Notes

Reaction equation

HRID 1703182 reaction equation
[Cl:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[CH:11](Br)([CH3:13])[CH3:12].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[Cl:1][C:2]1[N:6]([CH:11]([CH3:13])[CH3:12])[C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 785722-Chlorobenzimidazole

Product 1

HCID 130616971H-Benzimidazole,2-chloro-1-(1-methylethyl)-(9CI)

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-chlorobenzimidazole (2.0 g), isopropyl bromide (1.36 ml) and potassium carbonate (34 g) in dimethyl sulfoxide (200 ml) was heated at 60° C. for 6 hr and poured into ice. The resulting mixture was extracted with ethyl acetate and the extract was washed with water, dried over sodium sulfate and evaporated. The residue was chromatographed through silica gel using 5% methanol in dichloromethane. The appropriate fractions were evaporated to give 2-chloro-1-(1-methylethyl)benzimidazole, mp 58°-60° C.

Workup

  1. additionpoured into ice
  2. extractionThe resulting mixture was extracted with ethyl acetate
  3. washthe extract was washed with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customThe residue was chromatographed through silica gel using 5% methanol in dichloromethane
  7. customThe appropriate fractions were evaporated

Sources & evidence

ORD record
ord-8e07dae1026b40f1be7216d5bfb21786
Source dataset
uspto-grants-1982_09
Patent number
US04351832

Reaction notes

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