Eastman-kodak Company

Chang K Kim

Joan C Potenza

Francesco DeBellis

David Hoke

Robert F Romanet

William T Gruenbaum

Charles Warren Wright

Robert John Opitz

Michael E Campbell

David L Allen

John E Leary, Jr

Cataldo A Magguilli

Wayne N Lamicela

There are described intermediates for the preparation of known pyrazoloazole photographic magenta dye forming couplers and processes for making and using these intermediates. The intermediates are low molecular weight compounds represented by the structure: ##STR1## wherein: R, X, R.sup.1 and Y are defined herein. The process for making these intermediates involves diazotizing a 5-amino-1H-pyrazole to produce a 5-diazo-1H-pyrazole, then condensing the diazotized product with an active methine or methylene compound having a pKa of 14 or less to produce a substituted hydrazone and then subjecting the hydrazone to cyclization and reduction, in either order.

Intermediates for the preparation of pyrazoloazole photographic

A cyan pigment, bis(phthalocyanylalumino)tetraphenyldisiloxane is prepared in a single reaction mixture. A phthalonitrile is reacted at high temperature with an aluminum salt in the presence of an ammonia donor such as urea, in an inert, high boiling organic solvent. The resulting reaction product is cooled and without isolation, refluxed in an aqueous solution of a pyridine compound containing dichlorodiphenylsilane. The desired cyan pigment is then isolated.

Synthesis of bis(phthalocyanylalumino)tetraphenyldisiloxanes

A process for the desulfurization, and halogenation of a 1-acyl-7-acylthio-3,6-disubstituted-1H-pyrazolo[5,1-c]-1,2,4-triazole first compound comprises reacting the compound with an excess of a halogenating agent whereby a 3,6-disubstituted-7,7-dihalo-1H-pyrazolo[5,1-c]-1,2,4-triazole compound is formed.

Oxidative desulfurization and halogenation of thioacylated

The invention provides a process for making a thioether compound having the formula:

Manufacture of thioether compounds

Mono-acylated hydrazines are prepared in high yield by reaction of a hydrazine salt with an azole derivative of acyl halide in the presence of a strong base. Useful hydrazine salts include those of the formula RNHNH.sub.2 .multidot.HX, where R is alkyl, aryl, aralkyl, acyl, aroyl, heterocyclic or heteroaryl, and HX is a mineral or organic acid. Useful azole derivatives include those of the formula R'CO--A, where R' is alkyl, aryl, aralkyl, heterocyclic or heteroaryl and A is an azole radical such as pyrrole, imidazole, pyrazole, triazole, tetrazole, indole or benzimidazole.

Selective monoacylation of substituted hydrazines

Pyrazolotriazoles such as 3,6-disubstituted-1H-pyrazolo[5,1-c]-1,2,4-triazoles: ##STR1## are useful in the photographic arts, e.g. as magenta couplers. They may be made from 3,6-disubstituted-7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazines: ##STR2## by a two-step process. The first step comprises a ring contraction and a diacylation. The second step comprises hydrolysis of the acyl groups and desulfurization. The second step is conducted using an aqueous mixture of a hydrohalic acid such as hydrochloric acid and hypophosphorous acid, H.sub.3 PO.sub.2. When the hypophosphorous acid is used, less sulfur and sulfur-containing impurities are formed.

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Pittsford, NY, United States of America

Chang K Kim