1-Bromo-3-chloropropane → 1-(3-chloropropyl)-2-phenyl-1H-benzimidazole

HRID 2050249Notes

Reaction equation

HRID 2050249 reaction equation
[C:1]1([C:7]2[NH:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[O-].[Na+].Br[CH2:20][CH2:21][CH2:22][Cl:23]>CC(O)C>[Cl:23][CH2:22][CH2:21][CH2:20][N:11]1[C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[N:8]=[C:7]1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 128552-PhenylbenzimidazoleHCID 10942334Sodium Methoxide

Product 1

HCID 205062561-(3-chloropropyl)-2-phenyl-1H-benzimidazole

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 38.8 parts of 2-phenyl-1H-benzimidazole, 44 parts of a sodium methoxide solution 30% and 320 parts of 2-propanol is stirred and heated for 15 minutes at 50° C. After cooling, there are added 47.25 parts of 1-bromo-3-chloropropane. The whole is stirred and refluxed for 3 hours. The reaction mixture is evaporated. The residue is diluted with water and the product is extracted with methylbenzene. The extract is dried, filtered and evaporated, yielding 1-(3-chloropropyl)-2-phenyl-1H-benzimidazole as a residue.

Workup

  1. temperatureAfter cooling
  2. stirringThe whole is stirred
  3. temperaturerefluxed for 3 hours
  4. customThe reaction mixture is evaporated
  5. additionThe residue is diluted with water
  6. extractionthe product is extracted with methylbenzene
  7. customThe extract is dried
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-89ecc9ae2d224de6a40132b181c2bb6f
Source dataset
uspto-grants-1980_04
Patent number
US04200641

Reaction notes

Loading…