Hydrochloric Acid → 5-Chloro-2-pentyl-1H-benzimidazole-6-sulfonamide

HRID 904847Notes

Reaction equation

HRID 904847 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](O)(=O)[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]>[OH-].[NH4+]>[Cl:10][C:8]1[C:7]([S:11](=[O:13])(=[O:14])[NH2:12])=[CH:6][C:4]2[NH:5][C:15]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[N:2][C:3]=2[CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8892Hexanoic AcidHCID 132896884,5-Diamino-2-chlorobenzene-1-sulfonamide

Product 1

HCID 132897045-Chloro-2-pentyl-1H-benzimidazole-6-sulfonamide

Reagents, catalysts & solvents 1

HCID 14923Ammonium HydroxideSolvent

Procedure

To 50 ml of 4 N hydrochloric acid containing 11.8 g of 2-amino-4-chloro-5-sulfamylaniline was added 9.2 g of hexanoic acid and the suspension refluxed for 6 hours. Concentration in vacuo provided a solid which was then slowly added with stirring to 100 ml of 38% ammonium hydroxide. After collecting the solid by filtration, the precipitate was added to 400 ml of methanol and the suspension brought to a boil. Charcoal was then added and the mixture filtered through filter paper, cooled, and filtered through Celite. Concentration in vacuo gave brown crystals which upon recrystallization from acetonitrile provided 2.6 g of product, mp 183°-185°.

Workup

  1. temperaturethe suspension refluxed for 6 hours
  2. concentrationConcentration in vacuo
  3. customprovided a solid which
  4. additionwas then slowly added
  5. customAfter collecting the solid
  6. filtrationby filtration
  7. additionthe precipitate was added to 400 ml of methanol
  8. additionCharcoal was then added
  9. filtrationthe mixture filtered
  10. filtrationthrough filter paper
  11. temperaturecooled
  12. filtrationfiltered through Celite
  13. concentrationConcentration in vacuo
  14. customgave brown crystals which
  15. customupon recrystallization from acetonitrile

Sources & evidence

ORD record
ord-b1dbef019a09493fbee7c21c217459cf
Source dataset
uspto-grants-1983_12
Patent number
US04420487

Reaction notes

Loading…