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

HRID 258953

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HRID 258953 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 6212Chloroform용매

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온도
62 °C

실험 절차

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.

후처리

  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.

출처 및 근거

ORD 기록
ord-026a36c5a88347948937c14bcbe3247e
출처 데이터셋
uspto-grants-1977_07
특허 번호
US04035407

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