Process for the preparation of 6-methyl-3,4-dihydro-1,2,3-oxathi

Details Process for the preparation of 6-methyl-3,4-dihydro-1,2,3-oxathi Process for the preparation of 6-methyl-3,4-dihydro-1,2,3-oxathi

1986-08-29

1989-02-21

Ford, John M.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D29106

Patent

active

048066397

ABSTRACT:
6-Methyl-3,4-dihydro-1,2,3-oxathiazin-4-one 2,2-dioxide is prepared by cylcizing acetoacetamide-N-sulfonic acid or its salts with an at least approximately equimolar amount of SO.sub.3 in the presence of a water-immiscible, inert organic solvent and, if appropriate, also an inert, inorganic solvent. In the event that an equimolar amount of SO.sub.3 is employed, working up is effected by adding aqueous sulfuric acid when the cyclization reaction is complete; in the event that the amount of SO.sub.3 employed is more than equimolar, the 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-one 2,2-dioxide obtained in the form of the SO.sub.3 -adduct is hydrolyzed by adding water or ice, whereby sulfuric acid is formed from the SO.sub.3 combined in the SO.sub.3 -adduct.
The inert, organic solvent is then removed from the resulting multi-phase mixture by distillation, and the 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-one 2,2-dioxide is obtained in a pure form from the remaining aqueous sulfuric acid phase by crystallization. Additionally, quite generally, crude 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-one 2,2-dioxide is purified by recrystallization from aqueous sulfuric acid. The non-toxic salts of 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-one 2,2 dioxide--in particular the potassium salt--are valuable synthetic sweetening agents.

REFERENCES:
Fieser et al., Textbook "Organic Experiments", Heath and Co., Lex., MA, 1979, pp. 31, 32 and 34-38.
Clauss et al., Angewandte Chemie, Intl. Ed., 12, 869-876 (1973) ("Oxathiazinone Dioxides . . . ").
Petersen, Ber., 83, 551-558 (1950) ("Concerning New Reactions of Sulfamides").

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