Isobutyric Acid → 5-Chloro-2-(propan-2-yl)-1H-benzimidazole-6-sulfonamide

HRID 904849Notes

Reaction equation

HRID 904849 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)[CH:15]([CH3:17])[CH3:16].[OH-].[NH4+]>Cl>[Cl:9][C:7]1[C:6]([S:10](=[O:12])(=[O:13])[NH2:11])=[CH:5][C:3]2[NH:4][C:14]([CH:15]([CH3:17])[CH3:16])=[N:1][C:2]=2[CH:8]=1

Participants

5

Reactant 3

HCID 6590Isobutyric AcidHCID 14923Ammonium HydroxideHCID 132896884,5-Diamino-2-chlorobenzene-1-sulfonamide

Product 1

HCID 132897075-Chloro-2-(propan-2-yl)-1H-benzimidazole-6-sulfonamide

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
50 °C

Procedure

To 50 ml of 4 N hydrochloric acid containing 11.8 g of 2-amino-4-chloro-5-sulfamylaniline was added 7.0 g of isobutyric acid and the suspension refluxed for 6 hours. The mixture was concentraded in vacuo to a solid and the solid then added with stirring to 38% ammonium hydroxide and stirred for thirty minutes at 50° C. The solid was collected by filtration, air dried, dissolved in isopropanol, and charcoal added. After boiling for five minutes, the suspension was filtered, cooled, and then filtered through Celite. Recrystallization from isopropanol provided 2.0 g of off-white crystals, mg 256°-259°.

Workup

  1. temperaturethe suspension refluxed for 6 hours
  2. additionthe solid then added
  3. filtrationThe solid was collected by filtration, air
  4. customdried
  5. dissolutiondissolved in isopropanol
  6. additioncharcoal added
  7. filtrationthe suspension was filtered
  8. temperaturecooled
  9. filtrationfiltered through Celite
  10. customRecrystallization from isopropanol

Sources & evidence

ORD record
ord-d26d8f48b12e476fafb41cc85c8e4328
Source dataset
uspto-grants-1983_12
Patent number
US04420487

Reaction notes

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