SU281454A1 - METHOD FOR OBTAINING A MONO OR DISPOSED URINE - Google Patents

Description

This invention relates to a process for the preparation of MONO- or diuretic ureas, which have physiologically active properties and can be used in agriculture as pesticides and herbicides.

Methods are known for the preparation of mono- or disubstituted ureas by the reaction of pyromourea or isocyanate with an alkyl or ar or aminon.

In order to obtain physiologically active substances with increased activity, it is proposed to prepare a method for preparing previously unknown MONO- or disubstituted ureas of the general formula

R-YY-S-YY-S-SI SI, II / H

оR R

where R is hydrogen, unsubstituted phenyl or phenyl, having as a substituent a chlorine atom,

R and R are lower alknl, R and R, in addition, can form together with the carbon atom cycle.

The introduction of the acetyl group increases the physiological activity of the compounds obtained in comparison with the known alkyl- or aryl-substituted mono- or disubstituted ureas.

The proposed method is that the nitrourea or n-cyanate of the general formula RNCO, where R has the above value, is reacted with the corresponding substituted acetylene amine.

Data on the identification of the compounds obtained are given in table. 1 p 2.

Example 1. Preparation of N- (3,3-dimethylpronnn-1-yl) urea. 0.01 mol of 3-amipo-Zmethylbutin-1 is added to a solution of 0.01 mol of hydrochloride in 4 ml of water at room temperature. The reaction mixture is stirred at room temperature for

0.5 hour, then stirred at 50-55 ° C until the evolution of gas bubbles stops. The reaction mixture is filtered, the filtrate is slightly evaporated, upon cooling, precipitation of crystals is observed, which is recrystallized from water. Yield 70.7%; m.p. 151 ° C.

EXAMPLE 2. Preparation of N- (3-methyl-3-ethylpropium-1-yl) -urea. To a solution of 0.01 mol pitromochevipy in 4 ml of water at

the temperature is additional; 0.01 mol of 3-amino-Zmethyl-3-ethylpronin-1. The reaction mixture is stirred at room temperature for 0.5 hour, then at 50-55 ° C until the evolution of gas is stopped. The resulting reaction

The compound of General formula RNHCO-NHC-C -CHI, where R is hydrogen

Table 1

/ R R

Formations of crystals are observed, which are purified by recrystallization from water first, then from a mixture of benzene and petroleum ether. Yield 77.2%; m.p. 103 ° C.

Example 3. Preparation of N- (3,3-dimethylpropin-1-yl) -b1-phenylurea. To a solution of 0.88 g (0.01 uiol) 3-amino-3-methylbutin-1B, 3 ml of absolute benzene is added, with cooling, 1.1 g (0.01 mole of phenyl isocyanate) in small amounts. 5 minutes, crystals precipitate.The reaction mixture is heated to 40-50 ° C for 40 minutes, the mixture is cooled, strong crystallization is observed, remaining Compound of the general form of type RNHCO-NHC-C; 7; CH, where R-

the next night, then the benzene is evaporated and the resulting substance is recrystallized from heptane. The yield is 1.72 g (85.1%); m.p. 153 ° C. Example 4. Preparation of H- (3,3-dimethylpropin-1-yl) -L1 -. / And-chlorophenylurea. To a solution of 0.88 g (0.01 Ayul 3-amino-3-methylbutin-1 in 4 ml of absolute benzene, 1.5 ml (0.01 mol / 1 g-chlorophenyl isocyanate) are added in small portions while cooling. Immediately The white crystalline mass, which is heated to 40 ° C for 0.5 h, is cooled, benzene is evaporated and the resulting substance is not recrystallized from heptane. You yield 2.21 g (93.2%); T. Nl 144 ° C .

Table 2 / R R Phenyl or LH-Chlorophenyl

Subject invention

The method of obtaining mono - or disubstituted urea of the General formula

R — NH — C — NH — C — C CH,

OR R

where R is hydrogen, unsubstituted phenyl or phenyl, having as a substituent a chlorine atom,

R and R are lower alknl, R and R, in addition, can form together with the carbon atom a cycle,

characterized in that the nitrourea or isocyanate of the general formula RNCO, where R is as defined above, is reacted with an appropriately substituted acetylene amine.