Process for preparing benzisothiazole-1,1-dioxide and naphtho-1,

Details Process for preparing benzisothiazole-1,1-dioxide and naphtho-1, Process for preparing benzisothiazole-1,1-dioxide and naphtho-1,

1979-10-12

1981-03-31

Rizzo, Nicholas S.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548208, C07D27504

Patent

active

042594987

ABSTRACT:
This invention relates to certain 3,3,-di(4'-OP-carbocyclic aryl)-2,3-dihydrobenz[d]isothiazole-1,1-dioxides (and-2,3-dihydronaphtho[1,8-de]-1,2-thiazine-1,1-dioxides) and to the preparation thereof by reacting (a) at least 2 equivalents of (i) a 4'-OP-carbocyclic aryllithium compound wherein P is a protecting group compatible with organometallic reagents or (ii) a 4'-OP-carbocyclic arylMgE compound wherein P is a protecting group compatible with organometallic reagents and E is chloro, bromo or iodo and (b) 1 equivalent of a compound selected from a 3-chlorobenz[d]isothiazole-1,1-dioxide and a 3-chloronaphtho[1,8-de]-1,2-thiazine-1,1-dioxide to give the corresponding 3,3-di(4'-OP-carbocyclic aryl)-2,3-dihydrobenz[d]isothiazole-1,1-dioxide or the corresponding 3,3-di(4'-OP-carbocyclic aryl)-2,3-dihydronaphtho[1,8-de]-1,2-thiazine-1,1-dioxide, which compounds are useful in the synthesis of phenol and 1-naphthol sulfam(na)-phthaleins employed, for example, as photographic optical filter agents and filter agent precursors.

REFERENCES:
Mustafa et al., J. Chem. Soc., 1953, p. 1339-1340.
Abramovitch et al., J. Chem. Soc., "Perkin Trans. I", vol. 22, 1974, pp. 2589-2594.
Dutt, S., J. Chem. Soc., 121, 1922, pp. 2389-2394.
McOmie, J., "Protective Groups in Organic Chemistry", Plenum Press, N.Y., 1973, Chap. 4.

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