Acetic Acid → 5-Chloro-2-Methyl-6-Sulfamyl-1H-Benzimidazole Hydrochloride

HRID 904841Notes

Reaction equation

HRID 904841 reaction equation
Cl.[NH2:2][C:3]1[CH:9]=[C:8]([S:10](=[O:13])(=[O:12])[NH2:11])[C:7]([Cl:14])=[CH:6][C:4]=1[NH2:5].[C:15](O)(=O)[CH3:16]>>[ClH:14].[Cl:14][C:7]1[C:8]([S:10](=[O:13])(=[O:12])[NH2:11])=[CH:9][C:3]2[NH:2][C:15]([CH3:16])=[N:5][C:4]=2[CH:6]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 132896884,5-Diamino-2-chlorobenzene-1-sulfonamide

Product 1

HCID 204778575-Chloro-2-Methyl-6-Sulfamyl-1H-Benzimidazole Hydrochloride

Procedure

To 10 ml of 4 N hydrochloric acid containing 0.86 ml of acetic acid was added 2.22 g. of 2-amino-4-chloro-5-sulfamylaniline (VI) and the mixture refluxed for four hours. Concentration in vacuo gave a blue solid which was collected by filtration, dissolved in methanol, treated with charcoal and filtered. The blue solution was concentrated in vacuo and triturated with ether to yield a blue solid. Washing with methanol provided the product as light blue crystals which upon drying gave 1.0 g. of 5(6)-chloro-2-methyl-6(5)-sulfamyl-1(3)H-benzimidazole hydrochloride, m.p. 313°-316° C.

Workup

  1. concentrationConcentration in vacuo
  2. customgave a blue solid which
  3. filtrationwas collected by filtration
  4. dissolutiondissolved in methanol
  5. additiontreated with charcoal
  6. filtrationfiltered
  7. concentrationThe blue solution was concentrated in vacuo
  8. customtriturated with ether
  9. customto yield a blue solid
  10. washWashing with methanol

Sources & evidence

ORD record
ord-98369326657942aca737b03fa8897ebb
Source dataset
uspto-grants-1983_12
Patent number
US04420487

Reaction notes

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