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Water → N-(3,4-dichloro-5-isothiazolecarbonyl)-N-(4-chlorophenyl)-4-methoxybenzenesulfonamide

HRID 49406
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 49406
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:4][CH:3]=1.[Cl:20][C:21]1[C:25]([Cl:26])=[C:24]([C:27](Cl)=[O:28])[S:23][N:22]=1.O>CN(C)C=O>[Cl:20][C:21]1[C:25]([Cl:26])=[C:24]([C:27]([N:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[S:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[O:28])[S:23][N:22]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 962WaterHCID 598671N-(4-Chlorophenyl)-4-methoxybenzenesulfonamideHCID 109768863,4-Dichloro-5-isothiazolecarbonyl chloride

Produkt 1

HCID 11408949N-(3,4-dichloro-5-isothiazolecarbonyl)-N-(4-chlorophenyl)-4-methoxybenzenesulfonamideAusbeute 36,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel
2×

Versuchsvorschrift

To a solution of N-(4-chlorophenyl)-4-methoxybenzenesulfonamide (1.98 g) in unhydrous N,N-dimethylformamide (20 ml) 60% sodium hydride (0.24 g) was added at room temperature. After stirring the reaction mixture at the same temperature for 1 hour, a solution of 3,4-dichloro-5-isothiazolecarbonyl chloride (1.1 g) in unhydrous N,N-dimethylformamide (10 ml) was added thereto dropwise. After finishing the addition, the reaction mixture was stirred at room temperature for 18 hours and poured into water. The mixture was extracted with ethyl acetate and the organic phase was washed with water and dried with unhydrous sodium sulfate. The crude product obtained by distilling off the solvent under reduced pressure was recrystallized from ethanol to obtain N-(3,4-dichloro-5-isothiazolecarbonyl)-N-(4-chlorophenyl)-4-methoxybenzenesulfonamide (0.89 g). mp 154-158° C.

Aufarbeitung

  1. additionthe addition
  2. stirringthe reaction mixture was stirred at room temperature for 18 hours
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe organic phase was washed with water
  5. dry with materialdried with unhydrous sodium sulfate
  6. customThe crude product obtained
  7. distillationby distilling off the solvent under reduced pressure
  8. customwas recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-3585ca59184a4e89bbba02979f2ff0d0
Quelldatensatz
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06706748B2

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