THIAZOLYL-PHTHALIDE COMPOUNDS THEIR MANUFACTURE AND USE

摘要

1490929 Thiazolylphthalalide compounds CIBA-GEIGY AG 31 Oct 1975 [14 Nov 1974] 45390/75 Heading C4P The invention comprises thiazolylphthalide compounds having the general formula wherein A is a p-aminophenyl radical of general formula a 3-indolyl radical of general formula or a 2-thiazolyl radical of the general formula in which formulae R 1 , R 2 , X 1 , X 2 , R1 1 and R1 2 are H, C 1 -C 12 alkyl, alkoxyalkyl having 2-8 C atoms, C 5 -C 6 cycloalkyl or optionally substituted benzyl or phenyl or each of R 1 + R 2 , X 1 + X 2 and R 1 1 + R 2 1 together with the N atom may form a hetero ring optionally containing a further hetero atom, Y 1 and Y 1 1 are H, C 1 -C 12 alkyl, C 5 -C 6 cycloalkyl, or optionally substituted benzyl or phenyl, V 1 is H, C 1 -C 12 -alkyl or alkoxy, or acyloxy having 2-12 C atoms, Z 1 is H, C 1 -C 12 alkyl, benzyl or #-cyanoethyl, Z 2 is H, C 1 -C 12 alkyl or phenyl and rings B and D may be substituted by halogen, nitro or amino optionally substituted by C 1 -C 6 alkyl. They are prepared by reacting 1 mole of a phthalic anhydride with, in optional sequence, 1 mole of a compound A-H and 1 mole of a thiazole compound of general formula wherein A, R 1 , R 2 , and Y 1 are as above. In a preferred method phthalic anhydride is reacted in equimolar ratio with a p-aminobenzene compound in presence of an organic solvent at 50-150‹ C and then in a second stage with a 5-aminothiazole compound at 10-100‹ C in presence of an acid condensing agent, e.g. acetic anhydride, sulphuric acid, zinc chloride or phosphoroxy chloride. The compounds are used in chromogenic pressure sensitive and thermoreactive recording systems.