Pyridine → HCID 18758681, compound

HRID 433338Notes

Reaction equation

HRID 433338 reaction equation
C([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11](Cl)(=[O:13])=[O:12])=[CH:7][C:6]=1[Cl:15])(=O)C.[S:16]([NH2:26])(=[O:25])([C:18]1[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][CH:19]=1)=[O:17].CN(C1C=CC=CN=1)C.N1C=CC=CC=1>CCOC(C)=O>[Cl:15][C:6]1[CH:7]=[C:8]([S:11]([NH:24][C:21]2[CH:22]=[CH:23][C:18]([S:16](=[O:25])(=[O:17])[NH2:26])=[CH:19][CH:20]=2)(=[O:12])=[O:13])[CH:9]=[CH:10][C:5]=1[NH2:4]

Participants

6

Reactant 4

HCID 1049PyridineHCID 5333SulfanilamideHCID 218852-DimethylaminopyridineHCID 2827493-Chloro-4-acetamidobenzene-1-sulfonyl chloride

Product 1

HCID 18758681HCID 18758681, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-acetamido-3-chlorobenzenesulphonyl chloride (2.68 g, 10.0 mmol), sulphanilamide (2.06 g, 12.0 mmol), dimethylaminopyridine (1.22 g, 10.0 mmol) and pyridine (2.40 ml, 10.0 mmol) in EtOAc (150 ml) was stirred at ambient temperature for 3 days. The solution was washed with 1.0M aqueous hydrochloric acid and brine, dried and evaporated to dryness. The residue was dissolved in ethanol (100 ml) and 2M aqueous sodium hydroxide (22.1 ml) was added. The mixture was heated at reflux for 4 hours and then cooled to ambient temperature and evaporated to dryness. Water (25 ml) was added to the residue and the solution was neutralised to pH 7.0 by the addition of 1M aqueous hydrochloric acid. The aqueous solution was extracted with EtOAc, the EtOAc extracts washed with brine, dried and evaporated to give, as a solid, the title compound (2.34 g, 6.5 mmol). M.p. 197°-198°; NMR: 6.3 (s, 2H), 6.8 (d, 1H), 7.2 (s, 2H), 7.25 (d, 2H), 7.4 (dd, 2H), 7.55 (d, 1H), 7.65 (d, 2H); MS: 360.

Workup

  1. washThe solution was washed with 1.0M aqueous hydrochloric acid and brine
  2. customdried
  3. customevaporated to dryness
  4. dissolutionThe residue was dissolved in ethanol (100 ml)
  5. addition2M aqueous sodium hydroxide (22.1 ml) was added
  6. temperatureThe mixture was heated
  7. temperatureat reflux for 4 hours
  8. customevaporated to dryness
  9. additionWater (25 ml) was added to the residue
  10. additionthe solution was neutralised to pH 7.0 by the addition of 1M aqueous hydrochloric acid
  11. extractionThe aqueous solution was extracted with EtOAc
  12. washthe EtOAc extracts washed with brine
  13. customdried
  14. customevaporated
  15. customto give, as a solid

Sources & evidence

ORD record
ord-55fc0f0efa9b4ca9843102205819b296
Source dataset
uspto-grants-2003_12
Patent number
US06667342B1

Reaction notes

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