Benzenepropanoic acid → 5-Chloro-2-(2-phenylethyl)-1H-benzimidazole-6-sulfonamide

HRID 904850Notes

Reaction equation

HRID 904850 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][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=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:14]([CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:1][C:2]=2[CH:8]=1

Participants

4

Reactant 2

HCID 107Benzenepropanoic acidHCID 132896884,5-Diamino-2-chlorobenzene-1-sulfonamide

Product 1

HCID 132897085-Chloro-2-(2-phenylethyl)-1H-benzimidazole-6-sulfonamide

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To 40 ml of 4 N hydrochloric acid containing 9.4 g of 2-amino-4-chloro-5-sulfamylaniline was added 9.5 g of hydrocinnamic acid and the mixture refluxed for 6 hours. The dark reaction mixture was concentrated in vacuo to a semi-solid which was then added with stirring to 200 ml of 38% ammonium hydroxide. After stirring for thirty minutes, the solid was collected by filtration and then suspended in 200 ml of water at 50° C. Upon stirring for thirty minutes, the product was collected by filtration, dissolved in methanol, and the solution treated with charcoal and boiled for five minutes. The suspension was cooled, filtered through Celite, and concentrated in vacuo to yield pink crystals. Recrystallization from acetonitrile provided 2.6 g of off-white crystals, mp 226°-228°.

Workup

  1. temperaturethe mixture refluxed for 6 hours
  2. customThe dark reaction mixture
  3. concentrationwas concentrated in vacuo to a semi-solid which
  4. additionwas then added
  5. stirringAfter stirring for thirty minutes
  6. filtrationthe solid was collected by filtration
  7. customsuspended in 200 ml of water at 50° C
  8. stirringUpon stirring for thirty minutes
  9. filtrationthe product was collected by filtration
  10. dissolutiondissolved in methanol
  11. additionthe solution treated with charcoal
  12. temperatureThe suspension was cooled
  13. filtrationfiltered through Celite
  14. concentrationconcentrated in vacuo
  15. customto yield pink crystals
  16. customRecrystallization from acetonitrile

Sources & evidence

ORD record
ord-0713b0bd235d4f57b888492d5e9ca4f5
Source dataset
uspto-grants-1983_12
Patent number
US04420487

Reaction notes

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