p-Tolylacetonitrile → 5-Chloro-2-[(4-methylphenyl)methyl]-1H-benzimidazole-6-sulfonamide

HRID 904858Notes

Reaction equation

HRID 904858 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].[CH3:14][C:15]1[CH:23]=[CH:22][C:18]([CH2:19][C:20]#N)=[CH:17][CH:16]=1>Cl>[Cl:9][C:7]1[C:6]([S:10](=[O:12])(=[O:13])[NH2:11])=[CH:5][C:3]2[NH:4][C:20]([CH2:19][C:18]3[CH:22]=[CH:23][C:15]([CH3:14])=[CH:16][CH:17]=3)=[N:1][C:2]=2[CH:8]=1

Participants

4

Reactant 2

HCID 76280p-TolylacetonitrileHCID 132896884,5-Diamino-2-chlorobenzene-1-sulfonamide

Product 1

HCID 132897225-Chloro-2-[(4-methylphenyl)methyl]-1H-benzimidazole-6-sulfonamideYield 11.2%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To 150 ml of 6 N hydrochloric acid was added 17.7 g of 2-amino-4-chloro-5-sulfamylaniline followed by the addition of 15.7 g of 4-methylbenzyl cyanide; the mixture was then refluxed for 9 hours. The precipitate was collected by filtration and added to 300 ml of concentration ammonium hydroxide. After stirring for ten minutes at ambient temperature, the solid was collected and then added to 300 ml of water and stirred at 40° C. for ten minutes. The crude product was collected and dissolved in 1 liter of methanol which was brought to a boil; after stirring for five minutes, charcoal was added, and stirring continued for ten more minutes. The mixture was then filtered through two sheets of filter paper and then through Celite. Concentration in vacuo provided a solid which upon recrystallization from acetonitrile provided 3.0 g of pink crystals, m.p. 214°-217°.

Workup

  1. temperaturethe mixture was then refluxed for 9 hours
  2. filtrationThe precipitate was collected by filtration
  3. additionadded to 300 ml of concentration ammonium hydroxide
  4. customthe solid was collected
  5. additionadded to 300 ml of water
  6. stirringstirred at 40° C. for ten minutes
  7. customThe crude product was collected
  8. dissolutiondissolved in 1 liter of methanol which
  9. stirringafter stirring for five minutes
  10. additioncharcoal was added
  11. stirringstirring
  12. filtrationThe mixture was then filtered through two sheets of filter paper
  13. concentrationConcentration in vacuo
  14. customprovided a solid which
  15. customupon recrystallization from acetonitrile

Sources & evidence

ORD record
ord-fec4c198bb9c4ee897536be67ba59420
Source dataset
uspto-grants-1983_12
Patent number
US04420487

Reaction notes

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