Synthesis of substituted sulfam(na)phthaleins

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

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544135, 544368, 546 94, 548207, 2602455, C07D27902, C07D27506

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active

042107520

ABSTRACT:
The present invention is concerned with synthesizing certain ##STR1## by reacting (a) a 3,3-disubstituted sulfam(na)phthalein wherein one of the 3-substituents is a 4'-hydroxy-1'-phenyl moiety or a 4'-hydroxy-1'-naphthyl moiety substituted in the 3'-position with a perhalomethylcarbinol group and (b) an acid halide, ##STR2## wherein W is chloro or bromo and Y is hydrogen or an electron-withdrawing group, preferably, in the presence of a zeolite molecular sieve or acid alumina to give (c) the corresponding ##STR3## The compounds produced are useful, for example, as pH-sensitive indicator dyes or as photographic light-screening dyes.

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McClelland et al., "J. Chem. Soc.," (1940), pp. 323-327.
Royals, "Advanced Organic Chemistry," p. 617.
McOmie, "Protective Groups in Organic Chemistry," (1973), pp. 145, 146, 157-159.
Beilstein's, "Handbuch der Organischen Chemie" vol. 27, p. 534.
Mustafa et al., "J. Chem. Soc." (1952), pp. 1339-1340.
Abramovitch et al., "J. Chem. Soc.," Perkin Trans I, 22, pp. 2589-2594 (1974).
Dutt, "J. Chem. Soc." 121, pp. 2389-2394 (1922).

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