4-Chloro-2-butanone → 2-(3-Oxobutyl)-1H-1lambda~6~,2-benzothiazole-1,1,3(2H)-trione

HRID 1284539

Reaktionsgleichung

Reaktionsgleichung von HRID 1284539
Cl[CH2:2][CH2:3][C:4](=[O:6])[CH3:5].[S:7]1([C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:11](=[O:12])[NH:10]1)(=[O:9])=[O:8].[Na]>CN(C)C=O>[O:6]=[C:4]([CH2:3][CH2:2][N:10]1[C:11](=[O:12])[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[S:7]1(=[O:9])=[O:8])[CH3:5]

Komponenten

4

Edukt 2

HCID 806084-Chloro-2-butanoneHCID 24181110Benzosulfinide sodium; Garantose sodium

Produkt 1

HCID 130591402-(3-Oxobutyl)-1H-1lambda~6~,2-benzothiazole-1,1,3(2H)-trioneAusbeute 86,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

9.0 g (76 millimoles) of 4-chlorobutan-2-one were slowly added dropwise to 10.0 g (50 millimoles) of sodium saccharin in 100 ml of absolute dimethylformamide, while stirring. The temperature was then gradually increased to 80° C., and the reaction mixture was stirred at this temperature for 5 hours, after which it was cooled. An excess of ice-water was added, and stirring was continued for a further hour. The precipitated solid was filtered off under suction, recrystallized from ethanol and dried in a drying oven under reduced pressure at 50° C. to give 10.9 g (86%) of N-(2-oxobut-4-yl)-saccharin of melting point 118°-119° C.

Aufarbeitung

  1. stirringthe reaction mixture was stirred at this temperature for 5 hours
  2. temperatureafter which it was cooled
  3. stirringstirring
  4. waitwas continued for a further hour
  5. filtrationThe precipitated solid was filtered off under suction
  6. customrecrystallized from ethanol
  7. customdried in a drying oven under reduced pressure at 50° C.

Quellen und Nachweise

ORD-Eintrag
ord-e7f692a0142d437890f7a7c8ff945789
Quelldatensatz
uspto-grants-1986_01
Patentnummer
US04563474

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