C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
260/309.1, 260/2
C07D 275/06 (2006.01) C07D 417/00 (2006.01) C07D 471/06 (2006.01)
Patent
CA 1110237
Abstract of the Disclosure 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-dihydro- naphtho[1,8-de]-1,2-thiazine-1,1-dioxides produced as intermediates in the above synthesis.
311907
Bloom Stanley M.
Borror Alan L.
Foley James W.
Polaroid Corporation
Smart & Biggar
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