SU353544A1 - The method of obtaining 1-aryl-3-alkyl-5-chlorohydantoins - Google Patents

Description

The invention relates to a method for the preparation of "new compounds - 1-aryl-3-alkyl-5 chloro-indantoins, which are of interest as f.iziologicheokoki active (Substances.

The method is based on the well-known reaction of replacing the hydroxy group “and halogen.

(The proposed method is 1-aryl-3-alkyl-5chlorhydantoins of the general formula

where X is H, C1, Me, MeO, NOs; n - 1 or 2; R - Ci-Cz - alkyl,

It is concluded that 1-aryl-3-alkyl-5-0 xydumants are treated with thionyl chloride.

Example 1. 1-Phenyl-3-: methyl-5-chlorhydantoin.

10 ml of thionyl chloride at 26 ° C are added to 1.03 g (0.005 g mol) of 1-phenyl-3-methyl-5-ca. Distilled yut

an excess of thionyl chloride, and the solid residue (L25 g) is non-recrystallized} 1 of a mixture of benzene and pentane in a ratio of 1:10. Obtain 1.06 g (95%) of the substance with mp. 109-111 ° C.

Found,%: N 12.48, 12.52; CI 15.93, 15.83; C 53.66, 53.34; H 4.30, 4.21.

SSHNEGS.

Calculated,%: N 12.46; C1 15.78; C, 53.47; H 4.04.

0

Anaply

1-phenyl-3-ethyl-51, 3,4-dichlorophenyl-3-methylchlorohydantoin, 5-x hydropyne and others were obtained.

Example 2. 1 -. "- Chlorophenyl-3-methyl-55 chlorhydantoin.

4.81 g (0.02 g mol) of 1-l "-chlorophenyl-3-methyl-5-oxigidintoin is mixed with 40 ml of thionyl chloride at 19 ° C and stirred at this temperature iB for 2.5 hours after

What is left of the reaction mixture is overnight. Thionyl chloride is distilled off in a water jet pump vacuum, the residue crystallizes. It is washed with hexane and recrystallized from a mixture of benzene and petroleum ether (1:15). 5.71 g are obtained (89.1% of theory). Substances with m. Pl. 87-88 ° C.

methyl-0-chlorohydanto. in.

Example 3. 1-l-Tolyl-3-methyl-5-chlororgndantoin.

A mixture of 1.5 g (0.068 g of lyul) of 1-p-tolyl-3-methyl-5-oxyhydro} 1toin and 10 ml of thioNyl chloride is stirred for 40 minutes at 20-22 ° C until complete solution of the precipitate. The residue and after the solvent were distilled were recrystallized from hexaium. Obtain 1.4 g (86.5%) of substance with so pl. 102-104 ° C.

Naidio,%: N 10.91, 11.09.

CnHnNaClOs.

Calculated,%: N 10,81.

Analogychio receive 1-7I-tolyl-1-o-chlorphenyl-3-Methyl-5-chlorohidaetoy.

Example 4. 1-Parachloroethiyl-3-methyl-5 chlorohydantoin.

1.5 g (0.065 g mol) of 1-parachloro-thiyl-3-methyl-5-hydroxyhitoite are dissolved in 25 ml of thionyl chloride at 15 ° C, maintained at this temperature for 45-60 minutes, after which an excess of thioH1 the residue is washed with petroleum ether.

Obtain 1.4 g (84.8%) of substance with m. Pl. 119-121 ° C.

Naidio,%: N 12.00, 11.88. SshPaMgSYOZ. Calculated,%: N 11,74. Similarly, 1-l-yitrofeyl-Zmethyl-5-chlorohydride-tonne is obtained.

Subject invention

The method of obtaining 1-aryl-3-alkyl-5-chlorohydroxy compounds of the general formula

// l

N In

SI

si

Cl

where X is P, CI, Me, MeO, NOj;

n - 1 or 2;

R - Cl-Cz - alkyl,

characterized in that 1-aryl-3-alkyl-5oxyhydantoins are treated with thiopyl chloride.