SU362012A1 - - Google Patents

Description

The invention relates to a process for the preparation of a new asymmetric thiourea of the general formula N-C-JH II CH2 S where Alk is lower alkyl, R is aryl, cyan, R is H, alkyl. The proposed substances have valuable stabilization properties res. A known method for the preparation of substituted thioureas by the interaction of isothiocyanates with amines. The proposed method is based on the well-known chemical reaction-in, however, the use of M- (p-C-ethyl) p-alkoxyanilines as starting compounds, where R and alkyl have the aforementioned value, makes it possible to obtain new compounds with valuable properties. The proposed method consists in that aryl isothiocyanate is condensed with N- (3-R-ethyl) -n-alkoxyanilines in the medium of an organic solvent at boiling of the reaction mass and the products obtained are isolated by known methods. The IR spectra of the substances obtained contain absorption bands at 3385 cm (vNH), 1460 and 1330 cm- (and vc-N), which confirms their structure as derivatives of thiourea. Example 1. Getting S - (/ g-ethoxyphenyl) K-phenethyl-M-phenylthiourea. A solution of 6.75 g (0.05 g mol) of phenyl isothiocyanate in 15 ml of ethanol is added with stirring to a solution of 10.2 g (0.05 g-mol) of N-phenethyl-ethoxyaniline with 20 ml of ethanol and boiled in 5 ml of ethanol. hour in a water bath. The white crystalline precipitate which is precipitated upon cooling is filtered off, washed with ethanol, and dried. 11.75 g (70% of theory) of N- (p-ethoxyphenyl) -N-phenethyl-N-phenylthiourea are obtained in the form of white shiny crystals with m.p. 138.5-139.0 ° C. Recrystallization from alcohol does not increase the melting point. Found,%: C 73.60; H 6.25; N 7.52; S 8.57. C23H24N2OS. Calculated,%: C 73.37; H 6.42; N 7.43; S 8.51. Example 2. Getting 1M - ("- ethoxyphenyl) M-cyanoethyl-M-phenylthiourea. To a solution of 13.3 g (0.07 g-mol) of N-cyanoethyl-ethoxyaniline in 130 ml of benzene was added a solution of 9.46 g (0.07 g-mol} of phenyl isothiocyanate in 10 ml of benzene and boiled

4 hours in a water bath. The solvent is distilled off in vacuo; the residue in the form of a mobile oil is poured from n-hexane. The white precipitate that forms is filtered and dried. Obtain 16.1 g of a white powder with so pl. 61 - 64 ° C. By recrystallization from alcohol, 14.5 g (64% of theory) of N- (p-ethoxyphenyl) -M-cyanoethyl-X-phenylthiourea are obtained in the form of shiny, thin needles with a mp. 87-88 ° C. Re-recrystallization from alcohol raises the melting point to 90-91 ° C.

Found,%: C 66.86; H 5.87; N 13.10;

59.50. CisHisNsOS.

Calculated,%: C, 66.43; H 5.88; N 12.90; S 9.23.

Example 3. Preparation of H- (p-methoxyphenyl) -M-phenethyl-H-phenylthiourea.

To a solution of 20.0 g (0.088 g-mol} of N-phenethyl-i-methoxyaniline in 30 ml of ethanol was added 11.42 g (0.088 g-mol} of phenyl isothiocyanate in 20 ml of ethanol and boiled for 4 hours in a water bath The precipitate formed on cooling is filtered off, washed with ethanonol Nsushat. 29.4 g (93% of theory)., M - (“- megocx: ifenyl) - N-phenethyl-M-phenylurea in the form of white shiny crystals with mp. 156.5-157 ° C.

Found,%: C 72.19; H 6.09; N 8.68; S 8.60.

C22H22lN2OS.

Calculated,%: C, 72.89; H 6.11; N 7.72; S 8,84.

Example 4. Preparation of N- (/ g-methoxyphenyl) -M-phenethyl-L- (o-tolyl) -thiourea.

A solution of 13.11 g (0.088 mol of o-tolylisothiocyanate in 20 ml of ethanol was added to a solution of 20.0 g (0.088 mol} N-phenethyl / 7-methoxyaniline in 30 ml of ethanol. A white precipitate immediately formed. The suspension was boiled for 1 hour on a water bath, the precipitate is filtered off, washed with ethanol and dried to obtain 31 g (94% of theory) of L- (p-methoxyphenyl) -Y-phenethyl-N- (o-tolyl) -uremia in the form of bright needles with t mp 149.5-150 ° C.

Found,%: C 73.21; H 6.24; N 7.67; S 8.77.

C23H24N20S.

Calculated,%: C 73.37; H 6.42; N 7.43; S 8.51.

Subject invention

The method of obtaining M - (- alkoxyphenyl) (pK-ethyl) -arylthiourea of the general formula

-N -

MKO

II SNg S

SNG

I

AT

where Alk is lower alkyl,

R-aryl, cyangroup,

R - H, alkyl,

characterized in that M- (pK-ethyl) -ha-alkoxyaniline, where R has the indicated value, is reacted with aryl isothiocyanate in an organic solvent medium, followed by isolation of the target products by known techniques.