Methane → 5-chloro-2-ethyl-1H-benzimidazole-1-propanol

HRID 1413467Notes

Reaction equation

HRID 1413467 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].[C:14](O)(=O)[CH2:15][CH3:16].Cl.C>O>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]2[N:9]([CH2:10][CH2:11][CH2:12][OH:13])[C:14]([CH2:15][CH3:16])=[N:1][C:2]=2[CH:7]=1

Participants

6

Reactant 4

HCID 297MethaneHCID 313Hydrochloric AcidHCID 1032Propionic AcidHCID 30173573-((2-Amino-4-chlorophenyl)amino)propan-1-ol

Product 1

HCID 205063725-chloro-2-ethyl-1H-benzimidazole-1-propanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 30 parts of 3-[(2-amino-4-chlorophenyl)amino]-1-propanol, 20 parts of propanoic acid and 200 parts of a hydrochloric acid solution 4 N is stirred and refluxed for 3 hours. The reaction mixture is cooled, water and crushed ice are added and the whole is treated with activated charcoal. The latter is filtered off and the filtrate is alkalized with ammonium hydroxide. The product is extracted with methylbenzene. The extract is dried, filtered and evaporated. The residue is crystallized from 4-methyl-2-pentanone. The product is filtered off and dried, yielding 5-chloro-2-ethyl-1H-benzimidazole-1-propanol.

Workup

  1. temperaturerefluxed for 3 hours
  2. temperatureThe reaction mixture is cooled
  3. additionare added
  4. filtrationThe latter is filtered off
  5. extractionThe product is extracted with methylbenzene
  6. customThe extract is dried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue is crystallized from 4-methyl-2-pentanone
  10. filtrationThe product is filtered off
  11. customdried

Sources & evidence

ORD record
ord-150217a33d154f4bab7caa4025c910e4
Source dataset
uspto-grants-1981_02
Patent number
US04250176

Reaction notes

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