Hydrochloric Acid → 5-Chloro-2-(4-phenylbutyl)-1H-benzimidazole-6-sulfonamide

HRID 904854Notes

Reaction equation

HRID 904854 reaction equation
Cl.[NH2:2][C:3]1[CH:9]=[C:8]([Cl:10])[C:7]([S:11](=[O:14])(=[O:13])[NH2:12])=[CH:6][C:4]=1[NH2:5].[C:15]1([CH2:21][CH2:22][CH2:23][CH2:24][C:25](O)=O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[Cl:10][C:8]1[C:7]([S:11](=[O:13])(=[O:14])[NH2:12])=[CH:6][C:4]2[NH:5][C:25]([CH2:24][CH2:23][CH2:22][CH2:21][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[N:2][C:3]=2[CH:9]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 16757Benzenepentanoic acidHCID 132896884,5-Diamino-2-chlorobenzene-1-sulfonamide

Product 1

HCID 132897165-Chloro-2-(4-phenylbutyl)-1H-benzimidazole-6-sulfonamideYield 11.1%

Procedure

To 25 ml of 6 N hydrochloric acid was added 5.5 g of 2-amino-4-chloro-5-sulfamylaniline and 6.6 g of 5-phenylvaleric acid and the mixture refluxed for twenty-four hours. The gummy solid was collected by concentration in vacuo and then added to concentrated ammonium hydroxide. The suspension was stirred for twenty minutes, collected by filtration, and suspended in water at 50° C. The solid was collected by filtration, dissolved in methanol, brought to a boil, and charcoal added. The suspension was then filtered through two sheets of filter paper, cooled, and filtered through Celite. Recrystallization from acetonitrile provided 1.0 g of colorless crystals, m.p. 176°-180°.

Workup

  1. temperaturethe mixture refluxed for twenty-four hours
  2. customThe gummy solid was collected by concentration in vacuo
  3. additionadded to concentrated ammonium hydroxide
  4. filtrationcollected by filtration
  5. customsuspended in water at 50° C
  6. filtrationThe solid was collected by filtration
  7. dissolutiondissolved in methanol
  8. additionadded
  9. filtrationThe suspension was then filtered through two sheets of filter paper
  10. temperaturecooled
  11. filtrationfiltered through Celite
  12. customRecrystallization from acetonitrile

Sources & evidence

ORD record
ord-e79019f69cfb41ae91508f69855aecf3
Source dataset
uspto-grants-1983_12
Patent number
US04420487

Reaction notes

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