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Description

Method of producing 2-amino-5-nitrothiazole derivatives

one

This invention relates to a process for the preparation of new derivatives of 2-amino-5-nitro-thiazoles, which can be used as biologically active substances.

The use of the method of alkylation of secondary amines, which is widely known in organic chemistry, made it possible to obtain new thiazole compounds with valuable pharmacological properties.

The proposed method for the preparation of 2-amino-5-nitro-thiazole derivatives of the general formula

/ Rj

IN

/ NOzNAj-N C.

(sn, „

KL

R.

R4

where ODIN1 from the radicals Ri or R4 is a hydrogen atom and another of these radicals is a lower alkyl group with up to 3 carbon atoms;

Ra, Rs - hydrogen atom or methyl

Group;

n is the number O or 1,

or their acid addition salts, is that the compound of the general formula

tt

N J

0, N

CL ;.

R,

n

where Rg, Rs and p are as defined above, they are reacted with an alkylating agent, for example with an alkyl halide or with dialkyl sulfate. The reaction is carried out at an elevated temperature, better at 30-200 ° C. The target product is isolated or converted to an acid addition salt with an inorganic or organic acid in a known manner.

Example 1. 2 - (- Methyl-2-imidazolidinylidene) -amino-5-nitrothiazole.

2.13 g (0.01 mol) of 2- (2-imidazolidinylideneamino) -5-n-nitrotnazole together with 1.38 g (0.01 mol) of potassium carbonate are stirred up in a mixture of 1.41 g (0.01 mol) of methyl iodide and 80 ml of acetone (dried) and boil with reflux for 8 hours. After sucking the inorganic residue from the filtrate by chromatography on silica gel, 2- {1-methyl-2-imidazolidinylidene) amino-5-nitrothiazole was isolated.

T. pl. 204-206 ° C.

Example 2. 2- (1-Ethyl-2-imidazolidinylidene) -amino-5-nitrothiazole.

The compound was prepared analogously to example 1 from 2- (2-imidazolidinylideneamine) -5 nitrothiazole and ethyl iodide. The reaction mixture was partitioned on silica gel by thick layer chromatography.

T. pl. 174-175 ° C (decomposition).

Example 3. 4-Dimethyl-2-imidazolidinyl) -amino-5-nitrothiazole.

The compound was prepared analogously to example 1 from 2- (4-methyl-2-imidazolidinylideneamino) 5-nitrothiazole and methyl iodide.

T. pl. 200 ° C (decomposition).

Example 4. 2- (L-Methyl-2-imidazolidinylidene) -amino} -5-nitrothiazole hydrochloride.

1.2 g (0.0053 mol) of 2- (1-methyl-2-imidazolidinylidene) -amino-5-nitrothiazole is dissolved in 60 ml of methylene chloride and dry hydrogen chloride is added to the solution while cooling with ice and stirring. After a short time, colorless crystals are formed, which, however, soon again go into solution. The weak yellowish solution at 20 ° C is concentrated in vacuo and the precipitated crystals are sucked off. The crude product is washed with warm methylene chloride.

T. pl. 212 ° C (decomposition), at about 220 ° C - brown melt.

Yield 0.7 g (50% of theoretical).

LORDAMETA 3 ABOUT THEM: and

Claims (3)

1. A process for the preparation of 2-amino5-nitrotnazole derivatives of the general formula R. g . , where one of the 3 radicals Ri or R4 is a hydrogen atom and the other of these radicals is a lower alkyl group with up to 3 carbon atoms; Na, Nz - hydrogen atom or methyl Group; n 0 or 1, or their acid addition salts, characterized in that the compound of the general formula TO  -H ,) BUT where Kg, Ra and p are as defined above, are reacted with an alkylating agent at elevated temperature and the target product is isolated or converted to an acid addition salt in a known manner. 2. A method according to claim 1, characterized in that alkyl halide or dialkyl sulfate is used as the alkylating agent. 3. A method according to claim 1, characterized in that the alkylation is carried out at 30-200 ° C.