SU528870A3 - The method of obtaining the derivatives of 2-imidazolidinone or their salts - Google Patents

Description

where R, Ri, R2, Rs and X have the indicated value and Halo means chlorine or bromine atoms. The reaction is carried out in an anhydrous, inert under the reaction conditions, organic solvent, such as benzene, at 150-160 ° C.

Acetidines used are prepared in the manner described. The haloethyl imidazole derivatives of the formula I are obtained by cyclization of 2- (2-phenylaminethyl) -amino alcohol in the presence of phosgene, followed by alkaline hydrolysis of the resulting product and substitution of the hydroxy residue by a halogen atom using thionyl halide.

The compounds obtained are solids that are moderately soluble in water and highly soluble in dilute acids or in common organic solvents.

Example 1. 1- (l4-Chlorophenyl) -4-methyl-3 2- (3,3-dipropyl acetidine - 1 yl) - 1-methylethyl -2-imidazolidinone.

A mixture of 7 g of 3- (2-chloro-1-methylethyl) -1- (and lorofen) -4-methyl -2-imidazolidinop and 10 g of 3,3-dipropyl acetidine in 100 ml of anhydrous benzene is heated for 8 hours at 150 160 ° C in the bomb. The solvent is evaporated in vacuo and the residue is dissolved in water, brought to alkaline reaction with aqueous sodium carbonate and extracted with diethyl ether. The resulting residue is purified after the organic layer is concentrated by silica gel column chromatography using chloroform containing 8% methanol as eluent.

The yield of 8.6 g, because the cues. 220 ° C / 0.5 mmHg Art.

Example 2. 1 - (/ g-Chlorophenyl) -4-methyl-3-2 (3,3-dipropyl acetidine -1-yl) -1-methylethyl 2-imidazolidinone.

When using 3- (2-chloro-1-methylethyl) -1 (p-HL9rphenyl) -4-methyl-2-imidazolidinone instead of 3- (2-chloro-1-methylethyl) -1- (w-chlorophenyl), - 4-methyl-2-imidazolidinone in the method of example 1 receive the named compound, so Kip. 160 ° C / 0.6 mmHg Art.

Example 3. 1- (W-Chlorophenyl) -4-methyl-3-2 (3,3-dimethylacetidin-1-yl) -1-methyl ethyl -2-IMID. ZZOLIDINON.

Prepared according to destaine in example 4 from 3,3-dimethyl acetidine and 3- (2 chloro-1-methylethyl) -1- (f-chlorfepyl) -4-methyl 2-imidazolidinone, t.kip. 200 ° C / 0.6 mmHg Art.

The corresponding hydrochloride melts at 162-164 ° C.

Example 4. (p-Chlorophenyl) -amino-1-methylethyl-amino-1-propanol.

To a suspension of 38 g of lithium aluminum hydride in 2000 ml of diethyl ether cooled to 0 ° C, 95 g of ethyl ether (lhlorfepylcarbamyl) -ethylamino-propionic acid, dissolved in 1200 ml of anhydrous diethyl ether, are added in portions with stirring.

It is then heated for 2 hours with stirring under reflux.

By adding water, decompose the resulting complex at 0 ° C. The mixture is stirred for 30 minutes at room temperature and the inorganic solids are removed.

by filtration. The ether solution is dried and evaporated. The residue obtained after distillation in the flask gives 76 g of the title compound, i.e. 170 ° C / 04 mm Hg Art., yield 98.5%.

The acetate obtained by treatment with acetyl chloride in acetic acid is boiled at 160 ° C / 0.5 mm Hg. Art.

In the same way get l-chlorophenyl derivative, so Kip. 170 ° C / 0.5 mm

Hg Art.

The corresponding acetate is boiled at 160 ° C / 0.5 mm Hg. Art.

Example 5. 1 - (n-Chlorophenyl) -3- (l-oxymethylethyl) -4-methyl-2-imidazolidinone.

To a mixture of 36 g of (p-chlorophenyl) -amino-1-methyl ethyl-amino-1-iropanol in 75 ml of toluene and 29 g of KOH in 250 ml of water cooled to 0 ° C, a solution of 22 g of phosgene in 75 ml of anhydrous toluene is added. The mixture is stirred for 90 mip and the alkaline reaction is maintained by the addition of KOH solution. The toluene is separated and the aqueous phase is extracted with diethyl ether. Organic solutions are collected, dried and koitseptriruyut.

the residue is dissolved in 500 ml of methanol and treated with 2.5 g of KOH.

The mixture was allowed to stand for 2 hours and, after evaporation of the methanol in vacuo, it was dissolved in water and acidified with dilute

hydrochloric acid. After extraction with ether, the residue obtained after evaporation of the solvent is purified by column chromatography on silica gel with elution with chloroform containing 1% methanol. Fractions

containing the product, collect and concentrate. The residue is washed with a small amount of isopropyl ether, filtered and then washed with petroleum ether. Yield 15.2 g (38%); m.p. 108-110 ° C.

Also get w-chloro-substituted ana, log, yield 63%; m.p. 75-77 ° C.

Example 6. 1- (p-Chlorophenyl) -3- (2-chloro-1-methyl-ethyl) -4-methyl-2-imidazolidinone.

To a solution of 16 g of 1- (p-chlorophenyl) -3- (1-hydroxymethylethyl) -4-methyl-2-imidazolidinone in 400 ml of anhydrous chloroform is added dropwise while moving 14.5 g of SOCb and the mixture is kept at 0 ° WITH. The mixture is heated for 45 minutes under reflux,

concentrated in vacuo and dissolved in benzene and again concentrated to dryness. Yield 15.1 g (94%) of the title compound, mp. 70-72 ° C (from diisopropyl ether).

The corresponding g-chlorophenyl-substituted compound is also prepared. Output 97%, t. Kip. 200 ° C / 0.5 mmHg Art.

According to the described method, compounds of the formula I are obtained, the values of R, Ri, Rj, Rs and

X which are listed in the table.

Claims (1)

Invention Formula The method of obtaining derivatives of 2-imidazolidinone formula I R - GC-CMt - SI, CH-N4, N ./ WITH where R, Rb R2 and Rs mean hydrogen atoms or lower alkyl residues with 1-4 carbon atoms and X means one or more halogen atoms, or salts thereof, characterized in that the compound of general formula II  - cHj I SI, SI -N Ni SP where R, Ri, X have the indicated meanings. Halo is a chlorine or bromine atom, subjected to interaction with acetidine general formula III / CIS / RI Us sn. where Rg, Ra have the indicated value, in an anhydrous, inert under the reaction conditions, organic solvent, for example benzene, at 150-160 ° С with the release target product in free in the form or in salt form.