Ethanethiol → Benzenesulfonamide

HRID 1063977Notes

Reaction equation

HRID 1063977 reaction equation
[H-].[Na+].C(S)C.Cl[C:7]1[CH:12]=[CH:11][C:10]([S:13]([N:16](C2C=C(Cl)C=CC=2Cl)[C@H](C)CCCBr)(=[O:15])=[O:14])=[CH:9][CH:8]=1>O1CCCC1>[C:10]1([S:13]([NH2:16])(=[O:15])=[O:14])[CH:11]=[CH:12][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 24758Sodium hydrideHCID 23401686HCID 23401686, compound

Product 1

HCID 7370BenzenesulfonamideYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
22 °C

Procedure

To a solution of NaH (0.025 g, 1.03 mmol) in tetrahydrofuran (2 mL) was added ethanethiol (0.096 g, 1.54 mmol), followed by 4-chloro-N-[2,5-dichlorophenyl]-N-[(R)-1-methyl-4-bromobutyl]benzenesulfonamide (0.500 g 1.03 mmol) under nitrogen at 0° C. The reaction was stirred overnight at 22° C. The mixture was quenched with H2° (3 mL), extracted with ethyl ether (2×10 mL), dried over Na2SO4, and filtered. The organic solvent was concentrated under reduced pressure. Silica gel chromatography (1:9, ethyl acetate:hexanes) afforded 0.460 g of 4-chloro-N-[2,5-dichlorophenyl}-N-[4-(ethylthio)]-1-(R)-methylbutyl]benzenesulfonamide as a yellow oil in 59% yield. LC/MS 466.

Workup

  1. customThe mixture was quenched with H2° (3 mL)
  2. extractionextracted with ethyl ether (2×10 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationThe organic solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-bb6ce47bc8e846028b8831049b33dc9c
Source dataset
uspto-grants-2005_11
Patent number
US06967196B1

Reaction notes

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