Hydrochloric Acid → 5-Chloro-2-Ethyl-6-Sulfamyl-1H-Benzimidazole

HRID 904845Notes

Reaction equation

HRID 904845 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][CH3:16].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]([CH2:15][CH3:16])=[N:1][C:2]=2[CH:8]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 1032Propionic AcidHCID 132896884,5-Diamino-2-chlorobenzene-1-sulfonamide

Product 1

HCID 132897025-Chloro-2-Ethyl-6-Sulfamyl-1H-BenzimidazoleYield 14.2%

Procedure

A mixture of 12.0 g of 2-amino-4-chloro-5-sulfamylaniline, 16.1 g of propionic acid, and 54.4 ml of 4 N hydrochloric acid was refluxed for 6 hours. The solid was collected by filtration, dissolved in boiling methanol, charcoal added, and the solution filtered through Celite. Upon adding to 38% ammonium hydroxide with stirring, a pink solid formed. This was collected by filtration, washed with hot water, air dried, and then recrystallized from acetonitrile to provide 2.0 g of crystals, m.p. 240°-242°.

Workup

  1. temperaturewas refluxed for 6 hours
  2. filtrationThe solid was collected by filtration
  3. dissolutiondissolved
  4. additionadded
  5. filtrationthe solution filtered through Celite
  6. additionUpon adding to 38% ammonium hydroxide
  7. customa pink solid formed
  8. filtrationThis was collected by filtration
  9. washwashed with hot water, air
  10. customdried
  11. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-ec70fbc3789a4486b769fba25a2321ee
Source dataset
uspto-grants-1983_12
Patent number
US04420487

Reaction notes

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