Triethylamine → 2-(2-Chloro-2-fluoroethylthio)-phenylsulfonamide

HRID 373448Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 373448
C(N(CC)CC)C.[SH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[S:15]([NH2:18])(=[O:17])=[O:16].[Cl:19][CH:20]([F:23])[CH2:21]Cl>CO>[Cl:19][CH:20]([F:23])[CH2:21][S:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[S:15]([NH2:18])(=[O:17])=[O:16]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 790041,2-Dichloro-1-fluoroethaneHCID 110415322-Sulfanylbenzene-1-sulfonamide

Produkt 1

HCID 190867512-(2-Chloro-2-fluoroethylthio)-phenylsulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 217.8 g of the triethylamine salt of 2-mercaptophenylsulfonamide obtained in accordance with Example P6 and 101 g of 1,2-dichloro-1-fluoroethane in 950 ml of methanol is stirred in an autoclave for 24 hours at a temperature of from +65° C. to +70° C. and for a further 24 hours at from +95° C. to +100° C. The reaction mixture is then concentrated by evaporation and the residue is stirred with water. By extracting with ethyl acetate, washing with water, drying over sodium sulfate, concentrating by evaporation and purifying the residue by chromatography with methylene chloride, 99.5 g (49.2% of the theoretical yield) of 2-(2-chloro-2-fluoroethylthio)-phenylsulfonamide having a melting point of from +88° C. to +89° C. are obtained.

Aufarbeitung

  1. concentrationThe reaction mixture is then concentrated by evaporation
  2. stirringthe residue is stirred with water
  3. extractionBy extracting with ethyl acetate
  4. washwashing with water
  5. dry with materialdrying over sodium sulfate
  6. concentrationconcentrating by evaporation
  7. custompurifying the residue by chromatography with methylene chloride, 99.5 g (49.2% of the

Quellen und Nachweise

ORD-Eintrag
ord-67ad857fc8ef44dab95c79a133459e47
Quelldatensatz
uspto-grants-1992_11
Patentnummer
US05163996

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