Sodium ethanethiolate → Benzenesulfonamide

HRID 1063976Notes

Reaction equation

HRID 1063976 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11](C2C=C(Cl)C=CC=2COC(=O)C)[C@H](C)CCCBr)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[S-]CC.[Na+]>CN(C=O)C>[C:5]1([S:8]([NH2:11])(=[O:10])=[O:9])[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 4459711Sodium ethanethiolateHCID 53747118HCID 53747118, compound

Product 1

HCID 7370BenzenesulfonamideYield 14%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
22 °C

Procedure

To a solution of 4-chloro-N-[5-chloro-2-(acetoxymethyl)phenyl}-N-[(R)-1-methyl-4-bromobutyl]benzenesulfonamide (1.00 g, 1.91 mmol) in DMF (4 mL) was added sodium thioethoxide (0.535 g, 7.63 mmol) under nitrogen at 0° C. The mixture was stirred overnight at 22° C. The mixture was quenched with H2O (3 mL), extracted with ethyl ether (2×20 mL), dried over Na2SO4, and filtered. The organic solvent was concentrated under reduced pressure. Silica gel chromatography (1:9 ethyl acetate:hexanes) afforded 0.123 g of 4-ethylthio-N-[5-chloro-2-(hydroxymethyl)phenyl]-N-[4-(ethylthio)]-1-(R)-methylbutyl]benzenesulfonamide as a yellow oil in 14% yield. MS (ESI+), 488 (M+H)+.

Workup

  1. customThe mixture was quenched with H2O (3 mL)
  2. extractionextracted with ethyl ether (2×20 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationThe organic solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-87e03c2026bd4771bf6b18c1f2265811
Source dataset
uspto-grants-2005_11
Patent number
US06967196B1

Reaction notes

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