Process for the preparation of chlorosulfate and sulfamate deriv

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

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549336, 549337, 549396, 549426, 549427, 549433, 549443, 558 48, C07D31178, C07D31194, C07D30906, C07C30902

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053877004

ABSTRACT:
A process for producing chlorosulfate and sulfamate esters of 2,3:4,5-bis-O-(1-methylethylidene)-.beta.-D-fructopyranose and (1-methylcyclohexyl)methanol is disclosed. The process involves a two step procedure involving in the first step reacting of an alcohol with sulfuryl chloride in the presence of a tertiary or heterocyclic amine base in a solvent selected from the group consisting of toluene, t-butyl methyl ether or tetrahydrofuran to produce a chlorosulfate intermediate, which is preferably stabilized by an aqueous wash and/or treatment with a base, and in the second step reacting of the resulting intermediate with an amine in a solvent selected from the group consisting of t-butyl methyl ether, tetrahydrofuran and lower alkanol.

REFERENCES:
patent: 4582916 (1986-04-01), Maryanoff et al.

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