Propyl mercaptan → 2-(Propylsulfanyl)benzene-1-sulfonamide

HRID 619901Notes

Reaction equation

HRID 619901 reaction equation
[OH-].[K+].[CH2:3]([SH:6])[CH2:4][CH3:5].Cl[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[S:14]([NH2:17])(=[O:16])=[O:15]>CN(C)C=O>[CH2:3]([S:6][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[S:14]([NH2:17])(=[O:16])=[O:15])[CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 7848Propyl mercaptanHCID 14797Potassium HydroxideHCID 814102-Chlorobenzenesulfonamide

Product 1

HCID 30188682-(Propylsulfanyl)benzene-1-sulfonamideYield 82.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of potassium hydroxide (85%, 12 gm, 0.2 mole) and n-propylmercaptan (18.1 ml, 0.2 mole) in 100 ml dimethylformamide at 90° C. was added a solution of 2-chlorobenzenesulfonamide (19.1 gm, 0.1 mole) in 100 ml dimethylformamide. The reaction mixture was heated to reflux for five hours, cooled, and the solvent was removed in vacuo. The residue was diluted with water, made acidic with concentrated hydrochloric acid and extracted with ether. The ether extracts were washed with water and brine, dried over MgSO4 and concentrated in vacuo to yield the crude product. Recrystallization from a suitable solvent such as toluene afforded 19 gm (82%) product: m.p. 58°-64°.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for five hours
  3. temperaturecooled
  4. customthe solvent was removed in vacuo
  5. additionThe residue was diluted with water
  6. extractionextracted with ether
  7. washThe ether extracts were washed with water and brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo
  10. customto yield the crude product
  11. customRecrystallization from a suitable solvent such as toluene

Sources & evidence

ORD record
ord-26f8d60233de4445b18e5353b1c3c2b4
Source dataset
uspto-grants-1989_04
Patent number
US04818277

Reaction notes

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