Tetrahydrofuran → HCID 12045135, compound

HRID 748484Notes

Reaction equation

HRID 748484 reaction equation
C1COCC1.[NH2:6][C:7]1[C:16]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:9]([CH3:21])[CH:8]=1.[H-].[Na+].[Cl:24][C:25]1[CH:38]=[CH:37][C:28]2[S:29][C:30]([S:33](Cl)(=[O:35])=[O:34])=[C:31]([CH3:32])[C:27]=2[CH:26]=1>CN(C=O)C>[Cl:24][C:25]1[CH:38]=[CH:37][C:28]2[S:29][C:30]([S:33]([NH:6][C:7]3[C:16]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:9]([CH3:21])[CH:8]=3)(=[O:34])=[O:35])=[C:31]([CH3:32])[C:27]=2[CH:26]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydride2×HCID 27357565-Chloro-3-methylbenzo(b)thiophene-2-sulfonyl chloride2×HCID 10586307methyl 4-amino-5-methanesulfonyl-2-methylbenzoate

Product 1

HCID 12045135HCID 12045135, compoundYield 45.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Into 10 mL of THF was dissolved 135 mg of methyl 4-amino-5-methanesulfonyl-2-methylbenzoate, followed by addition of 22 mg of sodium hydride (oily, 60%) at room temperature. After 20 minutes of stirring at the same temperature, 130 mg of 5-chloro-2-chlorosulfonyl-3-methylbenzo[b]thiophene was added at 0° C., followed by 1 hour of stirring at room temperature and 5 hours of heating under refluxing. Further, 1 mL of DMF, 22 mg of sodium hydride (oily, 60%) and 50 mg of 5-chloro-2-chlorosulfonyl-3-methylbenzo[b]thiophene were added and the mixture was heated under refluxing for 2.5 hours. After-confirmation of disappearance of the starting material, the reaction was terminated by adding saturated aqueous ammonium chloride solution at 0° C., followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and then dried over anhydrous sodium sulfate. The solvent was removed by evaporation and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=3/2) to obtain 102 mg of the title compound as colorless powder.

Workup

  1. additionwas added at 0° C.
  2. temperatureof heating
  3. temperatureunder refluxing
  4. temperaturethe mixture was heated
  5. temperatureunder refluxing for 2.5 hours
  6. customAfter-confirmation of disappearance of the starting material, the reaction was terminated
  7. additionby adding saturated aqueous ammonium chloride solution at 0° C.
  8. extractionfollowed by extraction with ethyl acetate
  9. washThe organic layer was washed with saturated brine
  10. dry with materialdried over anhydrous sodium sulfate
  11. customThe solvent was removed by evaporation
  12. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=3/2)

Sources & evidence

ORD record
ord-7986cca5b3f5487796002ffa6f6272fd
Source dataset
uspto-grants-2008_07
Patent number
US07399781B2

Reaction notes

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