Acetic Acid → 5-chloro-2-methyl-1H-benzimidazole-1-propanol

HRID 1413465Notes

Reaction equation

HRID 1413465 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[NH:9][CH2:10][CH2:11][CH2:12][OH:13].Cl.[C:15](O)(=O)[CH3:16]>>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]2[N:9]([CH2:10][CH2:11][CH2:12][OH:13])[C:15]([CH3:16])=[N:1][C:2]=2[CH:7]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 30173573-((2-Amino-4-chlorophenyl)amino)propan-1-ol

Product 1

HCID 205063575-chloro-2-methyl-1H-benzimidazole-1-propanol

Procedure

A mixture of 20 parts of 3-[(2-amino-4-chlorophenyl)amino]-1-propanol, 50 parts of acetic acid and 150 parts of a hydrochloric acid solution 4 N is stirred and refluxed overnight. The reaction mixture is cooled and evaporated. The residue is dissolved in water and the solution is alkalized with ammonium hydroxide. The product is extracted with trichloromethane. The extract is dried, filtered and evaporated. The residue is crystallized from a mixture of 4-methyl-2-pentanone and 2,2'-oxybispropane, yielding 5-chloro-2-methyl-1H-benzimidazole-1-propanol.

Workup

  1. temperaturerefluxed overnight
  2. temperatureThe reaction mixture is cooled
  3. customevaporated
  4. dissolutionThe residue is dissolved in water
  5. extractionThe product is extracted with trichloromethane
  6. customThe extract is dried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue is crystallized from a mixture of 4-methyl-2-pentanone and 2,2'-oxybispropane

Sources & evidence

ORD record
ord-4528c940a3264c8bba17fffffea36606
Source dataset
uspto-grants-1981_02
Patent number
US04250176

Reaction notes

Loading…