Acetic Acid → 5-Chloro-2-phenyl-1H-benzimidazole-6-sulfonamide

HRID 904840Notes

Reaction equation

HRID 904840 reaction equation
[NH2:1][C:2]1[CH:8]=[C:7]([S:9](=[O:12])(=[O:11])[NH2:10])[C:6]([Cl:13])=[CH:5][C:3]=1[NH2:4].C(O)(=O)C.[CH:18](=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(O)C>[Cl:13][C:6]1[C:7]([S:9](=[O:12])(=[O:11])[NH2:10])=[CH:8][C:2]2[NH:1][C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[N:4][C:3]=2[CH:5]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 132896884,5-Diamino-2-chlorobenzene-1-sulfonamide

Product 1

HCID 132896905-Chloro-2-phenyl-1H-benzimidazole-6-sulfonamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2.21 g. of 2-amino-4-chloro-5-sulfamylaniline (VI), 50 ml. of glacial acetic acid, and 1.05 g. of benzaldehyde was refluxed for 16 hours and then decanted into water. The precipitate was collected by filtration, dissolved in ethanol, treated with Darco, filtered through filter paper and then through Celite. Concentration in vacuo provided a solid which was dissolved in ethanol, filtered, and forced out with water. Treatment of this beige solid with boiling acetronitrile provided an off-white solid mp 314°-316°.

Workup

  1. additionA mixture of 2.21 g
  2. customdecanted into water
  3. filtrationThe precipitate was collected by filtration
  4. dissolutiondissolved in ethanol
  5. additiontreated with Darco
  6. filtrationfiltered
  7. filtrationthrough filter paper
  8. concentrationConcentration in vacuo
  9. customprovided a solid which
  10. filtrationfiltered

Sources & evidence

ORD record
ord-7fc57d6bab03450db9d0c82715c53068
Source dataset
uspto-grants-1983_12
Patent number
US04420487

Reaction notes

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