SU458127A3 - Method for producing 1,3,4-thiadiazolyl-5-urea - Google Patents

Description

A method for producing 1,3,4-thiadiazolyl-5-urea of the general formula is provided.

Nn. .

VL ANRI-OO-FC

3

where R is hydrogen, alkyl Ci- € 4, alkenyl C: - € 4, alkynyl Ci- € 4, cycloalkyl Cs-Ce, alknylmercapto-Ci-C4, alkenylmercaptoC-C4, alkynylmercapto-Ci- € 4, aralkylmercaptogroup, and aryl may be substituted by chlorine or nitro, alkylsulfoxy C) -C4, alkylsulfonyl Ci- € 4, aralkylsulfoxyl, aralkylsulfonyl, alkyloxy Ci- € 4 or H4CO (SP2) n S-rpynna,

where R4 is oxy-, alkoxy-, amino-, alkylamino, unsubstituted or substituted by chloro arylamino;

p 1-4;

RI is alkyl Ci- € 4;

Na-hydrogen or alkyl Ci-C3;

Cs - alkyl Ci-Cz.

A known method for producing 1,3,4-thiadiazolyl-5-urea is that 5 amino-1,3,4-thiadiazole is reacted with halohydric acid ester and the resulting urethane is treated with an amine. The proposed method is based on the well-known

method. However, the use of other urea derivatives as starting compounds allows obtaining new biologically active compounds with better properties. The method is that the urethane of the general formula

. NK

R-A J-lfRl-COHs

where R and Ri have the indicated meanings;

Rs is methyl or phenyl,

at elevated temperatures, they are reacted with an amine of the general formula

NM

20

R where R2 and Ra have the indicated meanings. The desired product is isolated by simple methods.

The interaction of these compounds is carried out predominantly in an inert solvent, in hydrocarbons, for example benzene, toluene; ethers, for example diethyl ether, dioxane, tetrahydrofuran; chlorohydrocarbons, such as methylene chloride, chloroform, carbon tetrachloride; ketones, such as acetone; esters, for example ethyl acetate; acetonitrile and dimethylformamide. The reaction temperatures range from 0 to 140 ° C, preferably from 10 to 120 ° C. In carrying out the process, the starting materials are used in a molar amount. The reaction mixture is processed in the usual way.

Example. A mixture of 39.1 g of phenyl ester of N-methyl-N- (2-tert-butyl-1,3,4-thiadiazolyl 5) carbamic acid and 22 ml of 35% aqueous methylamine solution in 100 ml of methanol is stirred for 2 hours at 40 ° C. The reaction mass is then poured into 500 ml of water, the crystals that form are sucked off and N- (2-TpeT-butyl-1,3,4-thiadiazolyl-5) -N is obtained, N is dimethylurea, 82%, so pl. (methanol).

Similarly receive 1,3,4-thiadiazolyl-5 urea, presented in the table.

Subject invention

The method of obtaining 1,3,4 - thiadiazolyl - 5 urea of the general formula

-t to -co-fg;

at

where R is hydrogen, alkyl Ci-C, alkenyl Ci-C4, alkynyl, cycloalkyl Cs-Се, alkyl mercapto-Ci-C4, alkenyl mercapto-Ci

Ct, alkynylmercapto-Ci-C4, aralkylmercapto group, the aryl being optionally substituted by chlorine or nitro, alkylsulfoxy Ci-C4, alkylsulphonyl Ci-C, aralkylsulfoxyl, aralkylsulfonyl, alkyloxy

Ci-C4 or (OH2) p3-group, 5 where R4 is an oxy, alkoxy, amino, alkylamino group, unsubstituted or substituted by arylamino chloro; p 1-4; RI is alkyl; Ci € 4; R2 is hydrogen or alkyl Ci-C3; Ra is alkyl Ci-C3, characterized in that the urethane of the general formula II ll fjR is CJOUt. 6 where R and Ri have the indicated values: CB is methyl or phenyl, is reacted with an amine of the general formula 5 to ilN Ra and RS have the indicated values, and the target product is isolated with a known principle.