SU306626A1 - METHOD OF OBTAINING CARBOXAMIDOTHIAZOLES - Google Patents

Description

The invention relates to the production of new compounds that can be used as fungicides, plant growth regulators, as well as in the synthesis of organic substances.

A method for the freezing of carbox.midothiazoles using the formula

R.

  R

Jyt 3

II

X-C C-C

SOHi

where X is the replaced nli unsubstituted alKilna primer;

RI is hydrogen, substituted for ni-nemen, 1 is a hydrocarbon-rich soil containing up to 12 carbon atoms;

Ra is substitutable, enna or non-direct; enna hydrocarbon} 1a group, contains, and up to 12 carbon atoms;

or X is a hint, enna, or unsubstituted alkyl group containing up to 8 atoms of carbon;

RI is hydrogen, substituted or unsubstituted hydrocarbon soil, containing up to 12 carbon atoms;

The method consists in the fact that the chloroignd of the corresponding 3-carboxylic acid

process

amyioma

/ R:

HN (where

R ,,

Ri have R.

chenn.

The process is preferably carried out in an organic solvent medium, such as chloroform. Products are isolated by a known method as a base or as its salts.

Example 1. Preparation of 2,4-dimethyl-5-o-fennlcarboxanilindiazol.

A solution of 25 t of tppoi11: 1chloride in 25 ml of chloroform is slowly added to an unremovable mixture of 32 g (0.204 mol) of 2,4-dimethyl-5thiazolcarboxylic acid, 16 g of niridnna and 100 ml of chloroform, containing between -5 and + 5 ° WITH. After uncoupling for 1.25-2; at n ° C, the precipitated chlorine nitrate niridi 1a is filtered off and washed with a small cup of cold chloroform. To the filtrate, evaporated in vacuo on a water bath with a temperature of up to half or one-third of the original volume, 100 ml of chloroform are added and the mixture is added in small portions to an ice-cooled stirring solution, 33 g (0.195 mol) of o-aminodiphile and 22 g of threeIl

ethylamine in 150 g of chloroform. The mixture is then heated to room temperature, 100 ml of water is added, shaken in a separatory funnel and separated. The aqueous layer is discarded, and chloroform is washed with successive water, diluted with an aqueous solution of sodium bicarbonate and again with water. The chloroform solution is evaporated, the solidified precipitate is dissolved in dilute hydrochloric acid, filtered and the solution is made alkaline with dilute ammonia. The precipitated tnazol is double crossed from ethanol-water. Obtain 24.5 g (yield 41%) of the product, so pl. 137-140 ° C.

Example 2. As in Example 1, 2,4-dimethyl-5-thiazolecarboxylic acid chloride and mopophenylamine give 2,4-dimethyl-5-carboxanilidothiazole.

Subject invention

1. The method of producing carboxamidothiazoles is;

N L With rm. -N

II II / s-s-N

RI

where X is a substituted or unsubstituted alkyl group;

RI is hydrogen, a substituted or unsubstituted hydrocarbon group containing up to 12 carbon atoms;

Ra is a substituted or unsubstituted hydrocarbon soil containing up to 12 carbon atoms;

or X is a substituted or unsubstituted alkyl group containing up to 8 carbon atoms;

RI is hydrogen, a substituted Il1a pln is an unsubstituted hydrocarbon soil containing up to 12 carbon atoms;

Ra-aryl, alkylcaryl halo-daryl containing up to 12 carbon atoms, differing in that the acid chloride corresponds to the corresponding 5-carbo / R.

New acid is treated with amino.m NK, R,

where RI, R2 are as defined above, followed by isolation of the products in the form of a base or its salts by notifying them.

2. The method according to n. 1, characterized in that the process is carried out in an organic solvent medium, for example chloroform.