Abstract:
Process for preparing 3,4-dihydro-1,2,3-oxathiazine-4-ones and their salts which comprises the addition of chlorosulfonylisocyanate to a Beta -ketocarboxylic acid tert.alkyl ester, conversion of the addition product obtained at temperatures of from 40* to 100*C by means of separation of CO2 and alkylene into the Beta -ketocarboxylic acid amide-Nsulfochloride, by cyclization of same in an aprotic diluent by means of separation of hydrogen chloride - either in the presence of acid-binding agents or by heating up to temperatures above 50*C - and by conversion of the reaction products obtained in known manner into oxathiazinones or salts thereof.
Abstract:
3,4-Dihydro-1,2,3-oxathiazinones, a new class of chemical compounds having a ring system being hitherto unknown, are obtained when reacting fluoro sulfonyl isocyanates with ketocompounds of alkynes. The compounds having low-molecular substituents are artificial sweetening agents and the derivatives having hydrophobic substituents are interfacial active agents. All of the new compounds are organic intermediates having a plurality of reactive groups.
Abstract:
3,4-DIHYDRO-1,2,3-OXATHIAZINONES ARE OBTAINED WHEN REACTING KETONES WITH ARYLOXYSULFONYL ISOCYANATES. THE COMPOUNDS HAVING LOW-MOLECULAR SUBSTITUENTS ARE ARTIFICIAL SWEETENING AGENTS AND THE DERIVATIVES HAVING HYDROPHOBIC SUBSTITUENTS ARE INTERFACIAL ACTIVE AGENTS. ALL OF THE NEW COMPOUNDS ARE ORGANIC INTERMEDIATES HAVING A PLURALITY OF REACTIVE GROUPS.
Abstract:
3,4-Dihydro-1,2,3-oxathiazinones, a class of chemical compounds having a ring system, are obtained by converting the enolether of a Beta -ketocarboxylic acid amide-N-sulfone to the enol and treating the enol with an aqueous base. The compounds and their salts are artificial sweetening agents. All of the compounds are organic intermediates having a plurality of reactive groups.
Abstract:
6-Methyl-3,4-dihydro-1,2,3-oxathiazine-4-one-2,2-dioxide is prepared by reacting an acetoacetic acid tert. alkyl ester with fluorosulfonyl-isocyanate, optionally in the presence of an aprotic diluent, transforming the addition compound obtained into the acetoacetic acid amide-N-sulfofluoride by splitting off carbon dioxide and alkene at 60* to 100*C. and effecting cyclization of the fluoride with aqueous lye.
Abstract:
6-Methyl-3,4-dihydro-1,2,3-oxathiazin-4-one 2,2-dioxide is prepared by (a) reacting, in an inert organic solvent, a salt of sulfamic acid, which is at least partially soluble therein, with at least approximately the equimolar amount of an acetoacetylating agent, in the presence of an amine or phosphine catalyst, and by cyclizing the acetoacetamide-N-sulfonate which is formed in this reaction, or the free sulfonic acid, (b) by the action of at least approximately the equimolar amount of SO3, where appropriate in an inert inorganic or organic solvent, to give 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-one 2,2-dioxide, which is produced in the form of the acid in this reaction; it is possible, if desired, to obtain from the acid form (c) the appropriate salts by neutralization with bases. The non-toxic salts - in particular the potassium salt - are valuable synthetic sweeteners.