SU113692A1 - Method for producing rhodacanine dyes - Google Patents

Description

xx

i by condensation of β-apilinomethylene-substituted derivatives of tnazolinone- (4) of the general structure II: monometininanin,

C, Hr-NH-CH

with quaternary salts of nitrogenous heterocyclic bases, containing their active methyl group, of general structure III:

in a mixture of pyridine acetic anhydride and triethylamine at room temperature; the reaction product is isolated by conventional means.

In formulas I, And and III:

g-residues of nitrogen-containing heterocyclic base, in particular, digidroquinoline and dihydropyridine;

7 / - residues of nitrogen-containing heterocyclic bases, in particular 1,5-diphylsilthiazole;

R, R, and H are alkyl or substituted alkyl groups;

X is the acid residue.

Example. To ethyl lepidine toluenesulfonate, obtained by heating 0.28 g of lepidine and 0.4 g of ethyl ester 1-p-toluenesulfonic acid, was added 1.2 g of the 3-allylG / Etm obtained in a known manner .-- 4, 5-d11fe 1 -4-keto-5 (anilinomethylene) thiazolinothiazolocyanine of methyl sulfate (Formula II, where R is C.iH5; K CrH5: 7.-residue 4 ..) is dIlfeiylthiazole, 6 liters of dry pyridine, 2.2 ml of acetic acid) and 1.4 ml of triethylamine. The mixture is heated until the starting materials are dissolved and then settled at normal temperature.

The next day, 200 ml of ether are added to the reaction mixture and after 3 hours the ether is drained from the precipitate; the precipitate is dissolved by heating in 60 L1L ethyl alcohol and 60 ml of a 10% aqueous solution of potassium bromide is added to this solution.

The Bhiiianuinii precipitate is filtered off and washed with water and alcohol and the crystals are cleaned: 1aiisp from a mixture of methyl and propyl alcohol. Output 0, U2 g 3-allyl -) - ztil-4, 5-difel11pl-4-keto-5 (G-ectl-digi-drohi prayed and dem-4-et 11L ideas) of tianolyiothiazolociaiibromide (formula I, where R is CsI- ,; R and K ethyl; /, is the residue of hiiolium (4) and z is the residue of 4, .- dipheylthi; yl). T. ll. 224 °. Maximum absorption in ethyl alcohol and GGB.

Dialogically sitesirovy 3,3-diethyl-4-keto-5 (G-ethyl-dihydrohiiolilidei-4-ethylide) thiazole and thiazolocyanine bromide has a maximum absorption of an alcohol solution of 666 mp. and 3-: allyl-3-ethyl-4, 5dife 1IL-4-keto-5 (1-ethyl dihydropyridylidene-2-ethylidene) thiazolinothiazolocyanne perchlorate has an absorption maximum of an alcohol solution of 607 tons of oil.

The subject of the invention. A method for producing rhodacyanin dyes of general structure I:

-sn -sn

Characterized by the fact that, in order to improve the yields and facilitate the purification of the final dye, 5-aniline methylene-substituted monomethium cyanines, thiazolinone derivatives- (4) of the general structure I

ib

z

about n x

hondeud with quaternary salts of nitrogenous heterocyclic bases containing the active methyl group, of the general structure 1P:

111

Where; z - residues of nitrogen-containing heterocyclic bases,

in particular dihydroquinoline and dihydropyrmdine; z-01-tata nitrogen-containing heterocyclic oxy-ny,

in particular, 4,5-diphenylthiisol; R, R, and R are alkyl or substituted alkyl groups;

X is the acid residue,

in a mixture of pyridine, acetic anhydride and triethylamine at room temperature, after which the reaction product is isolated by conventional means.