Process for the preparation of 1,2-benzoxathiine derivatives

Details Process for the preparation of 1,2-benzoxathiine derivatives Process for the preparation of 1,2-benzoxathiine derivatives

1984-10-01

1986-07-29

Jiles, Henry R.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549467, 544212, 544297, C07D32706, C07D30728

Patent

active

046032118

ABSTRACT:
A novel process for the preparation of 3,4-dihydro-2,2-dioxo-3-methyl-1,2-benzoxathiin-8-ylsulfonamide of the formula I ##STR1## reacting a 5-halo-2,3-dihydro-2-methylbenzo[b]furan of the formula II ##STR2## wherein Hal is chlorine or bromine, with chlorosulfonic acid to give a 6-halo-2,2-dioxo-3-methyl-1,2-benzoxathiin-8-ylsulfonyl chloride of formula III ##STR3## wherein Hal is chlorine or bromine, converting this sulfonyl chloride with ammonia into a 6-halo-2,2-dioxo-3-methyl-1,2-benzoxathiin-8-ylsulfonamide of formula IV ##STR4## wherein Hal is chlorine or bromine, dehalogenating this sulfonamide with hydrogen in the presence of a tertiary amine and a noble metal catalyst, and hydrogenating the resultant 2,2-dioxo-3-methyl-1,2-benzoxathiin-8-ylsulfonamide of formula V ##STR5## with hydrogen in the presence of a noble metal catalyst.

REFERENCES:
Clancy et al, C.A., vol. 79, 1973, 79:105159t.

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