SU1348337A1 - Method of producing 1-(2ъ,4ъ,6ъ-trichlorphenyl)-3-/3ъъ-/2ъъ,4ъъ-(di-tert-amyl)phenoxy-acetamido/benzamido/-4-(4""-methoxypheniazo)-5-pyrazolone - Google Patents

Description

The invention of ousosngs to an improved method of obtaining 1- (2, 4, 6-trichlorophenyl) -3- {s 13483372

1 2 (di-tert-amyl) phenoxyacetate amido benzamido} -4- (4-methoxyphenyl-azo) -5-pyrazolone of formula

СНзО- N N-r-ir HCO

-YNSOSN O-O-SzN-lg

CsHirtr (,)

which is used in the color photographic process as a purple masking component.

The purpose of the invention is to increase the yield of the target product of formula (I), I simplify the process for its preparation and

reduced consumption ratios for raw materials.

This goal is achieved by obtaining the target product (I) at a ratio of 1- (2, 4, 6-trichlorophenyl) -3- {3 -12, (di-tert-amyl) phenoxy-acetamido) benzamido} -5-pyrazolone ( II): pyridine: alcohol, equal to 1: 0.36-0.72: 70-74. Yield 78-91%. No further cleaning is required.

The invention is illustrated by the following examples.

Example 1 (prototype). 92 g of 1- (2, 4, 6 -trichlorophenyl) -3- - | 2, 4 - (di-tert-amyl) phenoxyacetamido 1-benzamido I-5-pyrazolone is dissolved in 1221 g (1.25 l) of pyridine. The solution is cooled to 0 ° C. At this time, a solution of diazonium, a solution of 19.4 g of p-anisidine in 250 g (250 ml) of water and 47.2 g (40 ml) of concentrated hydrochloric acid are prepared, cooled before and a solution of 11.2 g of sodium is added. nitrite in 100 g (100 ml) of water. The diazotization is carried out at a temperature not higher than 5 ° C. The diazonium solution is diluted with ZU4, Lg (LOO ml) of alcohol, treated with activated carbon and filtered.

The solution thus purified is added to the pyridine solution of the components at such a rate that the temperature is no higher than 10 ° C. Stirring is continued for 0.5 h after the diazorator is fully added and the temperature is raised to 25 ° C. The reaction mass is diluted with a double volume of water;

precipitation occurs in the form

resin. The liquid is decanted, and the resin is thoroughly washed with water. The gummy residue is dissolved in I578 g (2l) of boiling alcohol. The precipitated orange powder was isolated from the cooled solution, which was recrystallized from 80% alcohol. 70 g (63%) of the product is obtained, which is characterized by unusual

melting point characteristics. Various samples melt at 133-135; 149-152; 147-150 and 142-144 ° C, after sintering the sample at 138 ° C.

I

Example 2.B 30-liter

steel enameled reactor with stirrer and jacket for cooling (cooled ethylene glycol) was charged with 20514 g (26 l) of ethanol, 350 g of 1- (2, 4,6-trichlorophenyl) -3- {h - 2, 4 - (di- tert-amyl) phenoxyacetamido benzamido-5-pyrazolone, 127 g (130 ml) of pyridine (the ratio of the starting pyrazolone to pyridine is 1: 0.36) and stirred until a solution is obtained. Cool the solution to 0 ° C with ethylene glycol brine and p-methoxyphenyldiazonium chloride solution (prepared from a solution of 70.2 g p-anisideIn, 750 g water, 209.9 g - 178 ml of concentrated hydrochloric acid and 36.4 g of nitrous acid) sodium in 65 g of water at a temperature of 0-5 ° C). An orange precipitate components (1) fall out of solution. Stirring is continued for 3.5 hours and the precipitate is filtered off. It is washed with 3945 g (5 l) of alcohol and dried. Obtain 340 g (81% of theory) 1- (2, 4, L-trichlorophenyl) -3- {g -12, (di-tert-amyl) phenoxy-acettamido benomedo | -4- (4-methoxyphenylazo) - 5-pi-rasolone with so pl. 133-135 C.

Found,%: C 60, H 5.21; N 10.51, C1 13.30.

C., ", 4NJ)

Calculated,%: C 61, 06; H 5.39; N 10.42; C1 13.21.

- In the IR spectrum of component (I) (UR spectrometer, KBr tablets), there are observed bands of stretching and deformation vibrations of the CH and CH groups in the region 2970-2880, 1470-1460, 1380 cm, the band at 3415 cm,) 3270 and 3U85 cm I wHco Р 555. The presence of carbonyl groups C-0 is identified by strips at NH 1680 cm) p 1720 cm. The presence of the benzene ring - by bands (- (, 1430, 1500, 1580 and 1600 cm, the presence of a para-substituted benzene fragment - 820 and 755 cm. The izOO and 1255 cm bands indicate the presence of an oxygen atom in the benzene ring.

The spectrum confirms the structure of compound (I)

Example 3. Compound I is prepared according to Example 2 with the difference that pyridine is taken in the amount of 54 g (260 ml), i.e. at a ratio of - NII source pyrazolone: pyridine 1: 0.72. The output of 340 g (81%).

Example 4. Compound I is prepared according to Example L with the difference that alcohol is taken in the amount of

Editor N. Kishtulints Order 5163/24

Compiled by G. Zhukov Tehred M. Khodanych

Circulation 371 VNIIPI USSR State Committee

for inventions and discoveries 113035, Moscow, Zh-35, Raushsk nab., 4/5

Production and printing company, Uzhgorod, st. Project, 4

22092 g (28 l), i.e. when the ratio of the original pyrazolone: alcohol 1:74. Yield 330 g (78.6%) due to partial dissolution of component I in alcohol.

Thus, the proposed method for preparing compound I, in comparison with a known method, allows to increase the yield of the target product and simplify the process, as well as to reduce the expenditure ratios.

Formula of invention

The method of obtaining 1- (2, 4, 6-tri-chlorophenyl) -3- {3 -F 2, (di-tert-amyl) phenoxy-acetamido benzamido - -4- (4-methoxyphenylazo) -5-pyrazolone by azo coupling p-methoxy-phenyldiazonium with 1- (2, 4, 6-tri-chlorophenyl) -3- (3-2, (di-tert-amyl) phenoxy-acetylamido benzamido}, 5-pyrazolone in the presence of pyridine and an alcohol medium at 0-5 ° C, characterized in that, in order to increase the yield of the target product, simplify the method of production and reduce the consumption coefficients for raw materials, the reaction is carried out at a mass ratio of 1 (2, 4, b-trichlorophenyl) -3- (C 2, . (di- ret-amyl) benz amido fenoksiatsetilamido -5-pyrazolone: pyridine: alcohol of 1: 0,36-0,72: 70-74.

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Claims (5)

The form of drugs and invention 15 .. The method of obtaining 1- ( 2, 4, 6-trichlorophenyl) - 3- {3 -f 2 ', 4 - (di-tert-amyl) phenoxyacetamido Zbenzamido-4- (4'-methoxyphenylazo) -5-pyrazolone 20 by azo coupling of p-methoxy phenyldiazonium chloride with 1- (2,4,6-trichlorophenyl) -3- [3 '- [2 ', 4' - (di-tert-amyl) phenoxyacetylamido] benzamido}, 5-pyrazolone in the presence of pyrididium 25 on in an alcoholic medium at a temperature of 0-5 ° C, characterized in that, in order to increase the yield of the target product, simplify the method of preparation and reduce the consumption coefficients for raw materials, the reaction is carried out at a mass ratio of 1 = (2 4, b '-trichlorophenyl) -3- [3 ~ 12, 4' - (di-tert-amyl) phenoxyacetylamido] benzamido) -5-pyrazolone: pyridine: alcohol, 35 equal to 1: 0.36-0.72 : 70-74.