SU427017A1 - METHOD OF OBTAINING TIADIAZOLYLTIOKARBONATOV - Google Patents

Description

one

This invention relates to a process for the preparation of new thiadiazole derivatives having fungicidal properties.

A method for the preparation of thiadiazolylthiocarbonates of the general formula based on the known reaction of the interaction of T1Bi and memerophthalamide with chlorogolic acid esters is proposed.

SbN5-T -

 -s-c-OB

x s about

where R is alkyl, halocdalkyl,

aryl, alkylaryl;

X is an oxygen or sulfur atom; we interact with alkaline or amine salts of mercaptothiadiazolone or mercaptothiadiazolthione with chlorocarbonates in an aqueous medium of an organic solvent, preferably in an aqueous acetone solution, at 10-20 ° C, followed by separation of the target product by known techniques.

When (measures 1. 3- (4-Phenyl-5-thio1-1,3,4thiadiazolyl-2) -o-isopropylthiocarbonate.

Into the reaction flask equipped with a stirrer, an addition funnel, a thermometer and a reflux condenser, 30.6 g (0.25

mol) of isopropyl chlorocarbonate in 30 ml of acetone and a solution of 66 g (0.25 mol) of the potassium salt of mercaptothiadiazolthione in 500 ml of water is poured in at 10 ° C for 15 minutes, after which the reaction mixture is transferred i hour at room temperature. A light yellow precipitate of the desired product falls out. Yield 37 g (61.4%). By a double conversion of sulfuric ether, a white crystalline substance is obtained, mp. 94-95 ° C.

Found,%: C 46.43; H 3.8; N 8.99.

CiiHi2N2O2S3.

Calculated,%: C 46.13; H 3.88; N 8.97. Similarly, with the corresponding molar ratios of the starting components, the compounds shown in the table below are obtained.

Example 2. 5- (4-Phenyl-5-oxo-1,3.4-tnadiazolyl-2) -o-isopropylthiocarbonate.

1.23 g (0.1 mol) of isopropyl chlorocarbonate in 8 ml of acetone is introduced into the reaction flask of PO 1 and a solution of the sodium salt of mercaptothiadiazolone obtained from 21 g (0.1 mol) is added over 7 minutes at 10 ° C

3-fevil-5-mercapto-3,4-thiadiazolone, 4 g (0.1 mol) of caustic soda and 100 ml of water. The reaction mass was stirred for 1 hour at room temperature, then 40-50 ml of sulfuric ether was added to it and the organic layer was separated. With strong cooling, white crystals of the target product precipitate out of it. Output 1.5 g (50%), so pl. 41-42 ° C (from ether). Found,%: C 48.70; H 3.87; N 9.62; S 21.73.5 Ci2Hi2N2O3S2. Calculated,%: C 48.63; H 4.09; N 9.45; S 21.63. Compounds 11–15 obtained in the table below are obtained in a similar manner. Subject of the invention and (;. C- -RoRi, XS OI where R is alkyl, halo-idalkyl, aryl, alkylaryl; X is an oxygen or sulfur atom, characterized in that alkaline or amine salts aqueous medium or in the medium of an organic solvent with the subsequent isolation of the target product by known techniques.