Thiazine-1,1-dioxide and isothiazole-1,1-dioxide derivatives
AssigneePolaroid Corporation
InventorsStanley M. Bloom, Alan L. Borror, James W. Foley
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AssigneePolaroid Corporation
InventorsStanley M. Bloom, Alan L. Borror, James W. Foley
Estimating the term…
In one aspect, this invention relates to a method of synthesizing certain 3-(4'-OH-carbocyclic aryl)-3-(carbocyclic aryl)-2,3-dihydrobenz[d]isothiazole-1,1-dioxides (and -2,3-dihydronaphtho[1,8-de]-1,2-thiazine-1,1-dioxides) by reacting a 3-(4'-OP-carbocyclic aryl)-3-(carbocyclic aryl)-2,3-dihydrobenz[d]isothiazole-1,1-dioxide (or a 3-(4'-OP-carbocyclic aryl)-3-(carbocyclic aryl)-2,3-dihydronaphtho[1,8-de]-1,2-thiazine-1,1-dioxide) wherein P is a protecting group with a carboxylic acid halide in pyridine to yield the corresponding 2-carbonyl derivative followed by removing the protecting group with weak acid to give the product. Optionally, the acylation step may be carried out by sequentially reacting the starting compound with an alkali metal hydride to give the corresponding 2-alkali metal salt and then reacting with the carboxylic acid halide in a suitable inert organic solvent. The products produced comprise phenol and 1-naphthol sulfam(na)phthaleins useful, for example, as photographic optical filter agents and filter agent precursors. In another aspect, the present invention relates to the carbonyl-substituted and alkali metal-substituted 2,3-dihydrobenz[d]isothiazole-1,1-dioxides and 2,3-dihydronaphtho[1,8-de]-1,2-thiazine-1,1-dioxides produced as intermediates in the above synthesis.
A compound of the formula ##STR78## wherein P is a protecting group, R.sup.1 and R.sup.2 each are selected from hydrogen, alkyl, alkoxy, chloro and fluoro;
A compound as defined in claim 50 wherein X represents the atoms necessary to complete 2,3-dihydrobenz[d]isothiazole-1,1-dioxide.
The compound ##STR80##
The compound ##STR81##
The compound ##STR82##
The compound ##STR83##
The compound ##STR84##
The compound ##STR85##
The compound ##STR86##
The compound ##STR87##
The compound ##STR88##
The compound ##STR89##
The compound ##STR90##
Dependencies are inferred from the claim text.