Thiocyanic acid, chloromethyl ester → 3,4,5-Trichloro-N,N-dimethyl-2-((thiocyanomethyl)thio)benzenesulfonamide

HRID 258953

Reaction equation

HRID 258953 reaction equation
[Cl:1][C:2]1[C:3]([SH:16])=[C:4]([S:10]([N:13]([CH3:15])[CH3:14])(=[O:12])=[O:11])[CH:5]=[C:6]([Cl:9])[C:7]=1[Cl:8].C[O-].[Na+].Cl[CH2:21][S:22][C:23]#[N:24]>CO.C(Cl)(Cl)Cl>[Cl:1][C:2]1[C:3]([S:16][CH2:21][S:22][C:23]#[N:24])=[C:4]([S:10]([N:13]([CH3:14])[CH3:15])(=[O:11])=[O:12])[CH:5]=[C:6]([Cl:9])[C:7]=1[Cl:8]

Participants

6

Reactant 3

HCID 76755Thiocyanic acid, chloromethyl esterHCID 10942334Sodium MethoxideHCID 214192913,4,5-Trichloro-N,N-dimethyl-2-sulfanylbenzene-1-sulfonamide

Product 1

HCID 214192933,4,5-Trichloro-N,N-dimethyl-2-((thiocyanomethyl)thio)benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Conditions

Temperature
62 °C

Procedure

To a stirring mixture a 1.5 grams (0.0047 mole) of 3,4,5-trichloro-N,N-dimethyl-2-(mercapto)benzenesulfonamide in 80 milliliters of methanol at 25° C, was added 0.39 grams of sodium methoxide. The mixture was stirred for 15 minutes and thereafter 1.0 gram (0.009 mole) of chloromethylthiocyanate was added thereto and the mixture stirred at room temperature for 3 hours. At the end of this time period, the reaction mixture was filtered to remove the solids which had precipitated. The filtrate further heated at 62° C for 2 hours and after cooling, the solvent was reduced in volume by evaporation under reduced pressure. The solids were thereafter removed by filtration. Additional filtrations gave additional solids. The recovered solids were combined and dissolved in chloroform and filtered. The solvent was removed by evaporation under reduced pressure and the solid product which remained was air dried. The 3,4,5-trichloro-N,N-dimethyl-2-((thiocyanomethyl)thio)benzenesulfonamide product was recovered in a yield of 0.7 grams (40 percent of theoretical) and melted at 155°-156° C.

Workup

  1. stirringthe mixture stirred at room temperature for 3 hours
  2. filtrationAt the end of this time period, the reaction mixture was filtered
  3. customto remove the solids which
  4. customhad precipitated
  5. temperatureafter cooling
  6. customthe solvent was reduced in volume by evaporation under reduced pressure
  7. customThe solids were thereafter removed by filtration
  8. filtrationAdditional filtrations
  9. customgave additional solids
  10. filtrationfiltered
  11. customThe solvent was removed by evaporation under reduced pressure
  12. customdried
  13. customThe 3,4,5-trichloro-N,N-dimethyl-2-((thiocyanomethyl)thio)benzenesulfonamide product was recovered in a yield of 0.7 grams (40 percent of theoretical) and melted at 155°-156° C.

Sources & evidence

ORD record
ord-026a36c5a88347948937c14bcbe3247e
Source dataset
uspto-grants-1977_07
Patent number
US04035407

Linked notes

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