SU389096A1 - - Google Patents

Description

METHOD OF OBTAINING 3,4-DESIGNED

one

The invention relates to the preparation of novel imidazolo-2-2 derivatives possessing biological activity.

A known method for producing imidazolone-2 derivatives, substituted in the 4.5 position, by reacting a-amino ketoi with potassium cyanate. However, this aposome cannot obtain 3,4-disubstituted imidazolone-2.

The proposed method for the preparation of 3,4-disubstituted imidazolone-2 of the general formula

About j HN NKi

NS.SKg

where RI is alkyl, aryl or haloaryl;

Ra is alkyl or aryl,

is that a monosubstituted N-carbamoylaryl (alkyl) -a-amino ketone derivative is subjected to intramolecular condensation under the action of hydrogen chloride in an aqueous or aqueous-alcoholic medium. Target products are described in known ways.

Example 1. 3-methyl-4-phenylimidazolone 1-2.

a) 1.92 g (0.01 mol) of N-methylcarbamoylphenyl-a-amino ketone is dissolved in 10 ml of concentrated hydrochloric acid. Reactions

occurs with the release of heat. After 0.5 hours, the solvent and hydrogen chloride are removed in vacuo, the product is washed with water and crystallized from ethyl alcohol. The resulting 3-methyl-4-phenylimidazolone-2 has m. 165 ° C. Output 1.7 g (quantitative). Found,%: N 15.93, 15.82; C 68.84; H 5.90.

CioHioNgO

Calculated,%: N 16.09; C, 69.02; H 5.79.

b) 1.92 g (0.01 mol of N-methylcarbamoylphenyl-a-amino ketone is dissolved in 10 g of ethyl alcohol and treated with 10 ml of concentrated hydrochloric acid. After complete

After the dissolution of the precipitate, the solvent and hydrogen chloride are evacuated in a vacuum, and the product is treated in the same way as in p. a. The resulting product has so pl. 1G5 ° C and does not give depression when melted in a mixture with the preparation obtained in item a.

IR spectra: V-NH 3495 cm. V, -j-o 1690,

-N-C

NH

1810, 1730; v 1500 yr-.

NMR: 3.17; 6.60; 7.45; 10.30.

Example 2. 3,4-Diphenylimidazolone-2.

2.54 g (0.01 mol) of phenylcarbamoylphenyl-amino-ketone is treated with 10 ml of an aqueous solution of IMIDAZOLONA-2 concentrated hydrochloric acid (1: 1). The starting compound is completely dissolved and after 0.5 hours the reaction product precipitates. The yield of 2.3 g (98%). After schercrystallization from abs. Ethyl C: PI) of the mouth, the substance completely sublimates between 180 ° C and 230 ° C. Found,%: N 11.88, 11.94. CisHiaNsO. Calculated,%: N 11.85. IR spectrum; V-NH 3420 ate. 3440 about 1550, 1690, 1750 sl.s -; v nm 1550 cc-H 0.01 mol of phenylcarbamoylmethyl-a-amino ketone is treated with 10 ml of aqueous hydrochloric acid (1: 1). After filtering off the precipitate and recrystallization from ethanol, 3-phenyl-4-methylimidazolone-2 is obtained. Example 3. 3-o-Chlorfs | nil-4-phenylimidazolone-2. 2.88 g of M-o-chlorophenyl "arbamoylphenyl-ss-amnnoquatone" is dissolved in 10 ml of ethanol and the tide, 10-15 ml of oxygenated hydrochloric acid. After: 0.5 hour, the starting compound is dissolved, and after 1 hour, the starting compound condensates. The processing of the reaction product is similar to the treatment given in example 2. The resulting target product has a melting point of 200 206 ° C. Yield 90-95%. Found,%: N 10.17, 9.92; From 12.70. CisHiiNaOCl Calculated,%: N 10.34; C1 13.09. The following compounds were prepared in the same way: 3- / g-Chlorophenyl-4-phen-1-Ilimidazolone-2, m.p. 243 ° С, OUTPUT- 98-99%. Found,%: N 10.21; C, 66.69; And 4.66; C1 13.02; 13.75. CisHnNsOC Calculated,%: N 10.34; C, 66.55; H 4.09; C1 13.09. IR spectrum; V-NH 3420 el., 3450 cl-i; v xjO 1680, 1710 el-; V 1480 cm3-l-Chlorophenyl-4- | fe1NilimndazolON-2, t. Pl. 210 ° C (sublimated from 180 ° C), yield 95-97%. Found,%: N 10.7. CisHiiNaOCl Calculated,%: N 10.34. V-NH 3450 cl {-; vхО 1680, -m-сС NNH 1710 si {-; V 1480 cm. Subject of the invention. Method for the preparation of 3,4-disubstituted imidazolone-2 with the general formula HN NKi where Ri is alkyl, aryl or haloaryl; R2 is alkyl or aryl, characterized in that the monosubstituted derivative of M- (Carbamoylaryl (or alkyl) -aamiyuketone is subjected to intramolecular condensation under the action of hydrogen chloride in an aqueous or aqueous-alcoholic medium, followed by isolation of the target product by known techniques.