Chloroacetone → 2-(2-Oxopropyl)-1H-1lambda~6~,2-benzothiazole-1,1,3(2H)-trione

HRID 1284535Notes

Reaction equation

HRID 1284535 reaction equation
Cl[CH2:2][C:3](=[O:5])[CH3:4].[S:6]1([C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:10](=[O:11])[NH:9]1)(=[O:8])=[O:7].[Na]>>[CH2:2]([N:9]1[C:10](=[O:11])[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[S:6]1(=[O:8])=[O:7])[C:3]([CH3:4])=[O:5]

Participants

3

Reactant 2

HCID 6571ChloroacetoneHCID 24181110Benzosulfinide sodium; Garantose sodium

Product 1

HCID 7060332-(2-Oxopropyl)-1H-1lambda~6~,2-benzothiazole-1,1,3(2H)-trioneYield 74%

Conditions

Temperature
110 °C

Procedure

26 ml (324 millimoles) of chloroacetone were slowly added dropwise to 40.0 g (200 millimoles) of sodium saccharin, while stirring (exothermic reaction). The temperature was gradually increased to 110° 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 35.2 g (74%) of N-acetonylsaccharin of melting point 142°-143° C.

Workup

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

Sources & evidence

ORD record
ord-a991b3c86ee6412cad33205497637bda
Source dataset
uspto-grants-1986_01
Patent number
US04563474

Reaction notes

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