SU794007A1 - Method of preparing 5-aryl-4-carboxymethylimidazolones-2 - Google Patents

Description

one

This invention relates to a process for the preparation of new 5-aryl-4-carboxymethyl-imidazolones-2 of the general formula

К- СсН4- (; (- СООС н,

 I I

HM-rixKH

II Oh

where RH, CH3, which can be used as phase active substances or intermediate products for the synthesis of physiologically active substances.

A known method for producing 1H-imidazolone-2 derivatives, which consists in the interaction of the K-derivatives of the substituted cyanamides with methyl chloroacetoacetic acid ester 1.

The disadvantages of the method are the inaccessibility of the starting materials, the difficulty of working with the starting materials (the need to protect the reaction medium from moisture and oxygen) and the low yields.

The aim of the invention is to obtain new 5-substituted 4-carboxymethyl-imidazolones-2 containing in position 6 aryl substituent possessing valuable properties.

The goal is achieved by the fact that methyl

the esters of p-bromoaroylpyruvic acid are fused with an excess of 2 hours at 100-110 ° C.

The starting esters of p-bromomaroyl pyruvic acid are obtained by bromination of aroyl pyruvic acid esters.

Example 1. 6-Phenyl-4-carboxymethylimidazolone-2.

A mixture of 2.85 g (0.01 mol) of methyl ester of p-bromobenzoyl pyruvic acid

and 4.80 g (0.08 mol) of urea are fused in

for 2 h at 100-110 ° C. Reactionary

the mixture is washed with water, dried and get

1.4 g (61%) of a white crystalline substance with mp. 200-201 ° C (from alcohol).

Found,%: N 12.79.

CiiHioNsOs.

Calculated,%: N 12,84.

Example 2. 5- (Tolyl) - 4-carboxymethylimidazolone-2.

Similarly, from a mixture of 2.0 g (0.006 mol) of p-bromo- (tolyl) pyruvic acid methyl ester and 2.4 g (0.04 mol) of urea, 1.9 g (86.3%) of a crystalline substance are obtained. square 185-186 ° C (from alcohol).

Found,%: N 11.77.

C, 2H, 2M20z.

Calculated,%: N 12.06.

34

The structure of the compounds obtained is proven, ln (nn

but the data of IR, PMR spectra and mass-R-CeH-C- - 3

spectroscopy.

The proposed method is simple and allows

to obtain 5-aryl-4-carboxylmethylamine 5

Lones-2 in high yield from those available where RH, CH3, characterized in that, the starting compounds. ,

limidazolone-2 general formulas taken into account during the examination

794007

hail acid is fused

10 by dividing the target product.

1. Taguchi Takeo et al. “Chemistry Lett, 1974, No. 5, p. 401-404.

Claims (1)

Claim The method of obtaining 5-aryl-4-carboxymethylimidazolone-2 of the General formula " 5 O where R — H, CH ₃ , characterized in that the methyl esters of β-bromoaroylpyruvic acid are fused with an excess of urea at 100-110 ° C with the release of the target product.