Process for the manufacture of 2(3H)-benzothiazolones substitute

Details Process for the manufacture of 2(3H)-benzothiazolones substitute Process for the manufacture of 2(3H)-benzothiazolones substitute

1981-05-18

1984-01-31

Coughlan, Jr., Paul M.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548150, 548175, 546 80, 546165, C07D27768, C07D27784, C07D49702

Patent

active

044291345

ABSTRACT:
A process for the manufacture of a 2(3H)-benzothiazolone compound substituted in 3-position, or of a 2(3H)-naphthothiazolone compound substituted in 3-position which comprises treating a 2(3H)-iminobenzothiazoline compound substituted in 3-position or a 2(3H)-naphthothazoline compound substituted in 3-position with an alkali metal hydroxide or alkaline earth metal hydroxide in a solvent or diluent stable to alkalis, in the absence of water or with substantial exclusion of water, and cyclizing the alkali metal or alkaline earth metal salt of the ortho-mercapto-N-phenyl- or -naphthyl-urea compound substituted at the nitrogen atom so formed, optionally without intermediate isolation, by treatment with an acid to give the 2(3H)-benzothiazolone compound substituted in 3-position or the 2(3H)-naphthothiazolone compound substituted in 3-position. The process furnishes the final products with high yield and purity; waste water problems are excluded by this process.

REFERENCES:
patent: 4234513 (1980-11-01), Papenfuhs
patent: 4252963 (1981-02-01), Papenfuhs
patent: 4293702 (1981-10-01), Umemura et al.
Kurzer et al., J. Chem. Soc., pp. 230-236, (1962).
Journal of Medicinal Chemistry 18: 315 (1975), pp. 315-318, Horgan et al., "Hypotensive Activity of 3-Alkyl-2-iminonrnxoyhisxolines".

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