Sodium sulfide nonahydrate → 3,4,5-Trichloro-N,N-diethyl-2-sulfanylbenzene-1-sulfonamide

HRID 258952Notes

Reaction equation

HRID 258952 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[C:6]([Cl:9])[C:5]([Cl:10])=[CH:4][C:3]=1[S:11]([N:14]([CH2:17][CH3:18])[CH2:15][CH3:16])(=[O:13])=[O:12].O.O.O.O.O.O.O.O.O.[S-2:28].[Na+].[Na+]>CO>[Cl:8][C:7]1[C:2]([SH:28])=[C:3]([S:11]([N:14]([CH2:17][CH3:18])[CH2:15][CH3:16])(=[O:13])=[O:12])[CH:4]=[C:5]([Cl:10])[C:6]=1[Cl:9]

Participants

4

Reactant 2

HCID 73972Sodium sulfide nonahydrateHCID 214192982,3,4,5-Tetrachloro-N,N-diethylbenzene-1-sulfonamide

Product 1

HCID 123697313,4,5-Trichloro-N,N-diethyl-2-sulfanylbenzene-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a mixture of 50 grams (0.15 mole) of 2,3,4,5-tetrachloro-N,N-diethylbenzenesulfonamide in 400 milliliters of methanol at reflux was added over a period of 1/2 hour, a solution of 100 grams (0.42 mole) of sodium sulfide-nonahydrate (Na2S-9H2O) in 400 milliliters of methanol. After the addition was complete, the mixture was refluxed for 3 hours. At the completion of this reaction, the mixture was allowed to cool and the sodium chloride which precipitated, was removed by filtration. The filtrate was diluted with 1 liter of water and the water insoluble materials were removed by filtration. The filtrate was thereafter acidified with concentrated hydrochloric acid and the crude product, a pale yellow solid precipitated out. The product was recovered by filtration, dried and recrystallized from hexane. The 3,4,5-trichloro-N,N-diethyl-2-(mercapto)benzenesulfonamide product was recovered in a yield of 46.0 grams (100 percent of theoretical) and melted at 96°-99° C.

Workup

  1. temperatureat reflux
  2. additionwas added over a period of 1/2 hour
  3. additionAfter the addition
  4. temperaturethe mixture was refluxed for 3 hours
  5. customAt the completion of this reaction
  6. temperatureto cool
  7. customthe sodium chloride which precipitated
  8. customwas removed by filtration
  9. additionThe filtrate was diluted with 1 liter of water
  10. customthe water insoluble materials were removed by filtration
  11. customthe crude product, a pale yellow solid precipitated out
  12. filtrationThe product was recovered by filtration
  13. customdried
  14. customrecrystallized from hexane
  15. customThe 3,4,5-trichloro-N,N-diethyl-2-(mercapto)benzenesulfonamide product was recovered in a yield of 46.0 grams (100 percent of theoretical) and melted at 96°-99° C.

Sources & evidence

ORD record
ord-83be9329fb8442e29e945ee04a67a52d
Source dataset
uspto-grants-1977_07
Patent number
US04035407

Reaction notes

Loading…