Benzenesulfonyl chloride → HCID 11109986, compound

HRID 751411Notes

Reaction equation

HRID 751411 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[NH:5][C:6]2[C:11]([C:12]=1[CH:13]=[O:14])=[CH:10][CH:9]=[CH:8][CH:7]=2.[C:15]1([S:21](Cl)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(O)C>[C:15]1([S:21]([N:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:12]([CH:13]=[O:14])=[C:4]2[Cl:3])(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 3147912-chloro-1H-indole-3-carbaldehyde

Product 1

HCID 11109986HCID 11109986, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound is prepared in accordance with the procedure of O. Olton et al., Tetrahedron, 54 (1998), 13915-13928 as follows. Sodium hydroxide is added to a stirred solution of 2-chloro-1H-indole-3-carboxaldehyde (239 mg, 1.33 mmol) in ethanol (10 mL). After 2 hr, the solvent is removed and the solid residue is dissolved in acetone and treated with benzenesulfonyl chloride (0.25 mL, 1.96 mmol). Soon a solid precipitated. After stirring for 1.5 hr at room temperature, the reaction mixture is heated to reflux for 1.5 hr. After cooling, water is added and the reaction is extracted with dichloromethane. The combined dichloromethane layer is washed with brine, dried over sodium sulfate and concentrated to an oil that is purified by chromatography eluting with heptane-0 to 10% ethyl acetate. Product containing fractions are combined and concentrated to afford 1-benzenesulfonyl-2-chloro-1H-indole-3-carboxaldehyde (70 mg, 17% yield) as a yellow solid. MS 320 (M+H); NMR 10.09 (1H, s); 8.26 (1H, d, J=9 Hz); 8.15 (3H, m); 7.85 (3H, m); 7.56 (2H, m).

Workup

  1. customThe title compound is prepared in accordance with the procedure of O
  2. customthe solvent is removed
  3. dissolutionthe solid residue is dissolved in acetone
  4. customSoon a solid precipitated
  5. temperaturethe reaction mixture is heated
  6. temperatureto reflux for 1.5 hr
  7. temperatureAfter cooling
  8. additionwater is added
  9. extractionthe reaction is extracted with dichloromethane
  10. washThe combined dichloromethane layer is washed with brine
  11. dry with materialdried over sodium sulfate
  12. concentrationconcentrated to an oil that
  13. customis purified by chromatography
  14. washeluting with heptane-0 to 10% ethyl acetate
  15. additionProduct containing fractions
  16. concentrationconcentrated

Sources & evidence

ORD record
ord-db6ba97118a0455aba0f23959b94dcd4
Source dataset
uspto-grants-2008_07
Patent number
US07405300B2

Reaction notes

Loading…