SU338100A1 - The method of obtaining 1-aryl-3-alkyl-5- (alkyl) (aryl) carbamoyloxyhydantoin - Google Patents

Description

The invention relates to the preparation of new derivatives of carbamic acid, which can be used as biologically active compounds.

A known method for the preparation of carbamic acid esters by reacting isocyanate with alcohol.

The proposed method for the preparation of 1-aryl-Zalkyl-5- (alkyl) (aryl) carba.uploxyhydaptoine of the general formula.

where X is hydrogen, chlorine, methyl, methoxy or

nitro group; R is alkyl with 1-4 carbon atoms,

aryl;

R is alkyl with 1 to 3 carbon atoms; n - 1 or 2,

consists in the interaction of 1-aryl-3-alkyl-b-oxyhydantoin with an equimolar amount of isocyanate in the medium of an organic solvent, for example acetone, dioxane, tetrahydrofuran, in the presence of a catalytic amount of organic base with

the subsequent selection of the target product. famous tricks.

The method allows to obtain compounds with 5 valuable properties.

Example I. 1-Phenyl-3-methyl-5-carbamoyloxyhydantoins.

To a suspension of 2.06 g (0.01 g mol} 1-phenyl-3-methyl-5-oxyhydantoin in 30 ml of acetone, 0.85 g (0.01 g mol) of n-proplizociapate in 10 ml of acetone is added dropwise 2 drops of triethylamine at 20-22 ° C. The mixture is stirred for 1.5 hours and kept at 20 ° C for 20 hours. The solvent is distilled off, giving 2.7 g of an oily substance, which crystallizes upon the addition of hexane.

(96.2%), so pl. 122-123 ° C (from the NOL meta output).

N 14.69; 14.76; C 57, 57.80;

Found, H 6.10; 6.23.

CHH, 7N304.

Calculated,%: N 14.42; C, 57.72; H 5.88.

Under conditions similar to Example 1, by using dioxap or tetrahydrofuran as a solvent, the following compounds are obtained.

gidaptoin, yield 91%, so pl. (from methanol).

Found,%: N 15.78; 16.00; C, 54.53; 54.38; H 5.10; 5.20.

S.GNZNL.

Calculated,%: N 15.96; C, 54.75; H 4.98.

1-Phenyl-3-methyl-5-butylcarbamoploxyhydantoin, high yield 96.5%, so pl. 147.5-148 ° C (from methanol).

Found,%: N 14.69; 14.76; C 57.80; 57.57; H 6.13; 6.10.

C, 4H, -Mz04.

Calculated,%: N 14.42; C, 57.72; H 5.88. 1-Phenyl-3-methyl-5-methylcarbamoyloxygidoite, yield 98.8%; m.p. 174-175 ° C. Found,%: N 15.21; 15.20.

C, 3H, 5N304.

Vychpelepo,%: N 15,15.

Example 2. β-Feil-3-methyl-5-arylcarbamoyloxyhitoites.

To 2.06 g (0.01 mol) of 1-feiyl-3-methyl-5-oxyhydantoin, 30 ml of dioxap are added and a solution of 1.53 g (0.01 nol) of o-chlorophenyl isocyanate in 10 lm of dnoxane and 2- 3 drops of triethylamine. The temperature of the reaction mixture rises to 30 ° C. The mixture is stirred for 2 hours at 25 ° C, after which the solvent is distilled off, pentane is added and the precipitate is filtered off. 3.02 g (87%) of solid are obtained. mp 151 - 152 ° С (from methanol).

Found,%: N 11.82; 11.88; C1 9.90; 9.92.

C, bN14KzS104.

Calculated,%: N 12.08; C1 10.20.

The following compounds are prepared analogously.

1-Phenyl-3-methyl-5-ig-chlorfeiylcarbamoyloxyhydanthone, yield 82.5%, m.p. 178-179 ° C (from methanol).

Found,%: N 11.87; 11.95; C1 9.89; 9.84.

C, 6Hi4N3C104.

Calculated,%: N 12.08; C1 10.20.

1-Phenyl-3-methyl - 5 - ".. chlorophenylcarbamoyloxyhydantoin, yield 95.7%, so pl. 182-183 ° C (from methanol).

Found A: N 12.30; 12.20, C1 10.00; 9.98.

CisHuNsClO.

1Calculated,%: N 12.08; C1 10.20.

1-Phenyl-3-methyl-5-f - tolylcarbamoyloxyhidantoin, yield 83%, so pl. 168-169 ° C

Found,%: N 12.48; 12.47; C 63.80; 63.83; H 5.01; 5.04.

С, 8Н, 7Нз04.

Calculated,%: N 12.37; C, 63.70; H 5.05.

1-FeNil-3-methyl-5-lg - nitrophenylcarbamoyloxyhydantoin, yield 80%, so pl. 185-187 ° C.

Found,%: C 55.15; 55.18; H 3.85; 4.20; N 15.20; 15.09.

C, 7Hi4N406.

C, 7H, 4Ms04.

Calculated,%: N 12.96.

Example 3. 1-lg-Chlorophenyl-3-methyl-5 (alkyl) arylcarbamoyloxyhydaptoines. To a solution of 2 g (0.0083 g-mol} of 1-l4-chlorfepyl-3-methyl-5-oxyhydantoin in 30 ml of tetrahydrofuray, an equimolar amount of alkyl (aryl) isocyanate and 3 drops of triethylamine are added at 19-20 ° C (or niridine). The temperature of the reaction mixture rises by 2-3 ° C. The mixture is stirred for 2-3 hours, after which the solvent is evaporated, the residue is recrystallized from methanol.

The following compounds are prepared analogously.

1-lg-Chlorophenyl-3-methyl-5-methylcarbamoyloxyhydride, yield 90%, so pl. 140-141 ° C. Found,%: N 1.4.14; 14.16; C1 11.77; 11.78.

C, 2H, 2N3CI04.

Calculated,%: N 14,11; From 11.91.

 - m - Chlorophenyl - 3 - methyl - 5 - ethylcarbamoyloxyhydantoin, yield 99%, t. Il. 144-145 ° C (from methanol).

Naidio,%: N 13.30; 13.08; C1 11.16; 11.18.

C, ZN, 4KzS104.

Calculated,%: N 13.48; C1 1.37. 1-W-Chlorophenyl-3-methyl-5-pronylcarbamoyloxyhidaite, vykhop; 98%, so pl. 156-157 ° C

Found,%: N 12.86; 13.10; C1 10.85; 1086.

SiN1BYZ02S1.

Calculated,%: N 12.89; C1 10.88.

1-W-Chlorophenyl-3-methyl-5-phenylcarbamoyloxyhydantoin, 91.3% yield, t. Il. 145-146 ° C (from methanol).

Found,%: N 11.62; 11.42; C1 9.91; 9.79.

C | 7Hi4NsCI04.

Calculated,%: N 11.68; C1 9.85. 1-W-Chlorophenyl-3-methyl-5-o-chlorophenylcarbamoyloxyhydantoin, yield 82%, so pl. II -152 ° C.

Found,%: N 11.10; 10.89; C1 18.03; 18.19; C, 51.77; 51.77; H 3.45; 3.40.

С17Н | ЗЫзС1204.

Calculated,%: N 10.66; C117.98; C, 51.79; H 3.24.

1-Ig-Chlorophenyl-3-methyl-5-. "- chlorophenylcarbamoyloxyhydantoin, yield 98.7%,

T. Il. 151-152 ° C.

Found,%: N 10.76; 10.81; C1 17.93; 17.81.

C, 7Hi3NaCl204.

Calculated,%: N 10.66; C1 17.98. Subject invention

OCONHR

where X is hydrogen, chlorine, methyl, methoxy or

nitro group;

R is alkyl with 1-4 carbon atoms, aryl;

R is alkyl with 1 to 3 carbon atoms; n - 1 or 2,

characterized in that 1-arnl-3-alkyl-5-oxyhydantoin is reacted with an equimolar amount of isocyanate in an organic solvent medium in the presence of catalytic amounts of an organic base and the subsequent isolation of the target product by known methods.