SU438652A1 - The method of obtaining derivatives of 5-amino4-methylthiazolin-2-one - Google Patents

Description

one

The invention relates to a new method for obtaining not previously known thiazolin-2-one derivatives, which can be used in the pharmaceutical industry. A method for preparing 4-aminomethyl-2-alkyl (aryl) -thiazol by reacting 4 chloromethyl-2-alkyl (aryl) -thiazoles with amines .

A method for the preparation of 5-amino-4-methylthiazolin-2-derivatives of the general formula is proposed.

CH,

HN

/ Y

About s

where A is the residue of dialkylamine, cycloalkylamine or a b- or 7-membered saturated nitrogen-containing heterocycle, which may contain other heteroatoms — nitrogen or oxygen,

in that 4-chloromethylthiazolin-2-one is reacted with a secondary amine in an organic solvent medium, for example dioxane, at 15-70 ° C, followed by isolation of the target products in a known manner.

Example 1. In a solution of 5.98 g (0.04 mol) of 4-chloromethylthiazolin-2-one in 50 ml of dioxane

at 20-60 ° C, 0.1 mol of dry dimethylamine is passed through for 20 minutes. After dimethylamine hydrochloride precipitates, 30 ml of benzene is added, the mixture is cooled to 10 ° C, then filtered, the filtrate is evaporated in vacuo, and the residue is repeatedly crystallized from heptane. Obtain 1.6 g (25%) of 5-dimethylamino - 4 - methylthiazolin - 2 - she, so nl. 124- 126 ° C.

Found,%: C 45.95; H 6.65; N 17.92. Sbpucoz

Calculated,%: C 45,55; H 6.37; N 17.71. Example 2. To a solution of 7.48 g (0.05 mol) of 4-chloromethylthiazoline - 2-one in a mixture of 100 ml

7.3 g (0.01 mol) of diethylamine is added to benzene and 50 ml of dioxane and the mixture is kept at 60-70 ° C for 15 minutes, then cooled to 10-15 ° C, the mass is filtered, the filtrate is evaporated to volume ml, and the mass is filtered ,

the filtrate is evaporated, the residue is crystallized from ether and ethanol. Receive 4 g (43%) of 5-diethylamino-4 - methylthiazoline - 2-it, so pl. 88-89 ° C.

Found,%: C 51.16; H 7.69; N 15.05.

.

Calculated,%: C, 51.58; H 7.45; N 15.04. Example 3. To a solution of 5.98 g (0.04 mol) of 4-chloromethylthiazolin-2-one in 50 ml of dioxane was added 6.8 g (0.08 mol) of piperidine and

maintain the mixture for 15 minutes at 60-70 ° С

then filtered, the filtrate is evaporated in vacuo, the residue is extracted with boiling boppol, the benzene extract is evaporated and the residue is crystallized from benzene: hexane (1: 1). 3.2 g (40%) of 5-piperid, ino4-methylthiazolin-2-one, are obtained. 153-154 C. Found,%: C 54.10; H 7.17; N 13.77.

CgHuNsOS.

Calculated,%: C 54.54; H 7.12; N 14.14.

Example 4. To a solution of 2.99 g (0.02 mol) of 4-chloromethylthiazolin-2-one in 20 ml of dioxane was added 3.48 g (0.04 mol) of morpholine, the mixture was kept at 60-70 ° C. , then cooled to 10 ° C, filtered, the filtrate is evaporated in vacuo and the residue is crystallized twice from benzene. 2.82 g (70%) of 5-morpholino-4-methylthiazolin-2-one is obtained, mp. 183-186 ° C.

Paideno,%: C, 47.81; H 6.20; N 14.06.

CisHiaN OaS.

Calculated,%: C 48.00; H 6.05; N 14.00.

Similarly, the interaction of 4-chloromethylthiazolin-2-it with with the corresponding secondary amine receive:

5-Hexamethylenimino - 4 - methylthiazoline - 2on, t. Pl. 141 - 142 ° C (decomp.).

Paydeno,%: C 57.11; P 7,69; N 13.20.

Cioni6N20S.

Calculated,%: C 56.57; P 7.60; N 13.20.

5- (4-Methylpiperazino) -4 - methylthiazolin-2on, t. Pl. 171 -172 ° C (decomp.).

Paydeno,%: C, 51.34; P 7.41; iN 20.09.

CgnisNsOS.

Calculated,%: C 50.67; P 7.09; .N 19.70.

(o-Methoxyphenyl) - piperazino-4-methylthiazolin-12-one, so pl. 228-229 ° C (decomp.).

Paideno,%: C 59.46; P 6.40; N 13.49.

C, 5n, 9.N3O2S.

Calculated,%: C 59.00; П 6.27; N 13.76. Subject invention

The method of obtaining 5-amino-4methylthiazolin-2-one derivatives of the general formula

HN

CH,

S A

where A is a residue of a dialkylamine, cycloalkylamine or a 6- or 7-membered saturated nitrogen-containing heterocycle, which may contain other heteroatoms — nitrogen or oxygen, characterized in that 4-chloromethylthiazolin-2-one is reacted with a secondary amine in an organic solvent medium, for example dioxane, at 15-70 ° C, followed by isolation of the target products in a known manner.