Triethylamine → Acesulfame

HRID 1732098

Reaction equation

HRID 1732098 reaction equation
C(N(CC)CC)C.[C:8]([NH2:14])(=[O:13])[CH2:9][C:10]([CH3:12])=[O:11].Cl[S:16](F)(=[O:18])=[O:17]>>[CH3:12][C:10]1[O:11][S:16](=[O:18])(=[O:17])[NH:14][C:8](=[O:13])[CH:9]=1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 26159Sulfuryl chloride fluorideHCID 80077Acetoacetamide

Product 1

HCID 36573AcesulfameYield 46%

Procedure

A mixture, with a total volume of 50 ml, of 40.4 g (0.4 mol) of triethylamine and liquid SO2 was added dropwise, at -10° C., to a solution of 20.2 g (0.2 mol) of acetoacetamide and 23.7 g (0.2 mol) of chlorosulfonyl fluoride in 70 ml of liquid SO2. The mixture was stirred for 2 hours and the liquid SO2 was then distilled off, a vacuum being applied at the end. The residue was added dropwise to 400 ml of aqueous NaOH, acidified with concentrated hydrochloric acid, with ice-cooling, and extracted with ethyl acetate. After treatment of the ethyl acetate phase with animal charcoal and Na2SO4, the extract was evaporated in vacuo. 15 g (approx. 20% of theory) of 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-one 2,2-dioxide were obtained.

Workup

  1. distillationthe liquid SO2 was then distilled off
  2. additionThe residue was added dropwise to 400 ml of aqueous NaOH
  3. temperaturecooling
  4. extractionextracted with ethyl acetate
  5. customAfter treatment of the ethyl acetate phase with animal charcoal and Na2SO4, the extract was evaporated in vacuo

Sources & evidence

ORD record
ord-35384e460b1e4317b7aa20fbd63a113b
Source dataset
uspto-grants-1986_11
Patent number
US04625024

Linked notes

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