Butyric Acid → 5-Chloro-2-propyl-1H-benzimidazole-6-sulfonamide

HRID 904843Notes

Reaction equation

HRID 904843 reaction equation
[NH2:1][C:2]1[CH:8]=[C:7]([Cl:9])[C:6]([S:10](=[O:13])(=[O:12])[NH2:11])=[CH:5][C:3]=1[NH2:4].[C:14](O)(=O)[CH2:15][CH2:16][CH3:17].Cl>[OH-].[NH4+]>[Cl:9][C:7]1[C:6]([S:10](=[O:12])(=[O:13])[NH2:11])=[CH:5][C:3]2[NH:4][C:14]([CH2:15][CH2:16][CH3:17])=[N:1][C:2]=2[CH:8]=1

Participants

5

Reactant 3

HCID 264Butyric AcidHCID 313Hydrochloric AcidHCID 132896884,5-Diamino-2-chlorobenzene-1-sulfonamide

Product 1

HCID 132896975-Chloro-2-propyl-1H-benzimidazole-6-sulfonamideYield 40.5%

Reagents, catalysts & solvents 1

HCID 14923Ammonium HydroxideSolvent

Procedure

A mixture of 9.0 g of 2-amino-4-chloro-5-sulfamyl aniline, 14.1 g of butyric acid, and 40.3 ml of a 15% hydrochloric acid solution was refluxed for 6 hours and then concentrated in vacuo to a solid. The solid was dissolved in hot methanol, treated with charcoal, boiled ten minutes, and filtered. Concentration in vacuo provided a solid which was then added portionwise to 200 ml of concentrated ammonium hydroxide. The free base was then recrystallized from acetonitrile to yield 4.5 g of pink crystals, m.p. 230°-234°.

Workup

  1. temperaturewas refluxed for 6 hours
  2. concentrationconcentrated in vacuo to a solid
  3. dissolutionThe solid was dissolved in hot methanol
  4. additiontreated with charcoal
  5. waitboiled ten minutes
  6. filtrationfiltered
  7. concentrationConcentration in vacuo
  8. customprovided a solid which
  9. customThe free base was then recrystallized from acetonitrile

Sources & evidence

ORD record
ord-5fe44b07638d452295f58e86ec0cbf48
Source dataset
uspto-grants-1983_12
Patent number
US04420487

Reaction notes

Loading…