Ethanethiol → HCID 15766992, compound

HRID 232526Notes

Reaction equation

HRID 232526 reaction equation
[CH2:1]([SH:3])[CH3:2].[OH-].[K+].Cl[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[S:13]([NH2:16])(=[O:15])=[O:14]>CN(C)C=O>[CH2:1]([S:3][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[S:13]([NH2:16])(=[O:15])=[O:14])[CH3:2]

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 14797Potassium HydroxideHCID 814102-Chlorobenzenesulfonamide

Product 1

HCID 15766992HCID 15766992, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

62 g (1.0 mol) of ethanethiol were added to a mixture of 65.9 g (1.0 mol) of 85% strength potassium hydroxide powder and 500 ml of dimethylformamide at 25° C. while stirring, and stirring was continued for 15 minutes. Thereafter, a solution of 95.8 g (0.5 mol) of 2-chlorobenzenesulfonamide was added at 90° C. while stirring in the course of 30 minutes, and stirring was continued for 8 hours at 110° C. The mixture was cooled and was evaporated down under reduced pressure, after which the residue was partitioned between methylene chloride and water, and the organic phase was washed with dilute sodium chloride solution. Evaporating down under reduced pressure gave 88.4 g (81.5% of theory) of the title compound as a semicrystalline mass.

Workup

  1. stirringstirring
  2. stirringwhile stirring in the course of 30 minutes
  3. stirringstirring
  4. waitwas continued for 8 hours at 110° C
  5. temperatureThe mixture was cooled
  6. customwas evaporated down under reduced pressure
  7. customafter which the residue was partitioned between methylene chloride and water
  8. washthe organic phase was washed with dilute sodium chloride solution
  9. customEvaporating down under reduced pressure

Sources & evidence

ORD record
ord-3e35b02698ff411d844f6d5169bdedff
Source dataset
uspto-grants-1997_01
Patent number
US05591694

Reaction notes

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