SU271410A1 - METHOD OF OBTAINING 1-AMIDIN-3- (SUBSTITUTED PHENYL) -CARBAMIDE - Google Patents

Description

This invention relates to the field of carbamide production, which can be used in the medical industry. A method is proposed for the preparation of 1-amidine-3 (substituted phenyl) carbamide of the general formula V-NH-CO-NH-C where Yi is a halogen if or halogen, located in the 3 rd, as well as in the W and 5 and 5 positions; or Y4 is a trifluoromethyl or pitrityl group, if Y is hydrogen or halide, or a methyl group located in the 2nd or 3rd position; or Y is a nitro group, if. It is a trifluoromethyl group, or a halide, which is in the 3 position. The method consists in that the compound of the general formula 5 10 15 20 25 where y-i and Y have the values indicated above, is reacted with concentrated hydrochloric acid, followed by isolation of the target product in a known manner. Example. 4-Chloro-3-cyanoaniline (6.1 g), dicyandiamide (3.7 g), water (16 ml) and concentrated hydrochloric acid (3.6 ml) are heated under reflux for 30 minutes. After cooling, the crystallized hydrochloric acid compound is filtered off and washed with a small amount of water. The resulting “crude in terms of purity salt is dried and non-recrystallized from alcohol. 4-Chloro-3-cyanophenylbiguanide as a hydrochloric acid salt is separated in the form of white needles (6.4 g) with m.p. 233 ° C, the reaction is accompanied by the release of gas bubbles. The base is obtained as small white needles by basifying a solution of this salt with sodium oxide hydrate; after recrystallization from alcohol, the compound forms colorless prisms; m.p. 202 ° C. Melting is accompanied by release of bubbles. The base of biguanide (3.2 g) was dissolved in N-ethanesulfonic acid (32 ml) and maintained at a temperature of 90 ° C for 2 hours. For that

Medetansulfonat. The salt is collected after cooling (2.8 g) and recrystallized from methanol (or water). White needles are obtained, having a m. Pl. 210 C. The base is obtained by treating an aqueous solution of the salt with sodium hydroxide in the form of white needles; m.p. 222 ° C. The base can be further purified by recrystallization from alcohol. This substance is moderately soluble in water.

According to the method described for formula 1, the following compounds are prepared. Temperatures refer to melting points.

Additional examples

1.1-Amidin-3- (3-chloro-4-cyanophenyl) -carbamide; m.p. 213 ° C.

2.1-Amidin-2 (3,4-dichlorophenyl) -carbamide; m.p. 95-98 ° C.

3.1-Amidium-3 - (2-chloro-4-cyanophenyl) carbamide; T. Il. 210 ° C (with evolution of gas bubbles).

4.1-Amidin-3- (4-trifluoromethylphenyl) -carbamide; m.p. 173 ° C

5.1-Amidin-3- (4-chloro-3-nitrophenyl) -carbamide; m.p. 213 ° C (with the release of gas bubbles).

6.1-amidino-3- (4-chloro-trifluoromethylphenyl) -carbamide methanesulfonate; m.p. 239-240 ° С (with decomposition).

7.1-Amidine - 3- (2-cyanophenyl) - carbamide: t. Pl. 205 ° C (with the release of gas bubbles).

8.1-Amidin-3- (4-cyan-3-methylphenyl) -carbamide; m.p. 200.5 ° C.

9.1-Amidin-3- (2-bromo-4-cyanophenyl) -carbamide; m.p. 206 C (with the release of gas bubbles).

10.1-Amidine-3 - {4-cyano-2-methylphenyl) carbamide; m.p. 171 ° C.

11.1-Amidine - 3- (3,4,5-trichlorophenyl) -carbamide; m.p. 180.5 ° C (with the release of gas bubbles).

12.1-Amidin-3- (3-chloro-4-nitrophenyl) - carbamide methanesulfonate; m.p. 241 ° С (with decomposition).

13.1-Amidin-3- (4-nitro-3 - trifluoromethyl) carbamide; m.p. 202 ° C (with the release of gas bubbles).

14.1-Amidin-3- (4-cyan-3-fluorophenyl) -carbamide with the release of gas bubbles.

Subject invention

The method of obtaining 1-amidin-3- (substituted phenyl) -carbamide of General formula

NH NH-CO NH-Cf.

Nhz

where Y is a halogen if Y is a trifluoromethyl, nitrile or nitro group located in the 3rd position, or a halogen located in the 3rd position and also in the 3rd and 5th position;

or Y is trifluoromethyl or nitrile pears, if Y is hydrogen, or halo, or methyl gruppa, which are in the 2nd or 3rd position;

or Y is a nitro group, if the Y is trifluoromethyl group, or a halide that is in the 3rd position, characterized in that the compound of the general formula

, NH N} t-C (MH) NH-cf

Shg

where Y and Y have the above meanings, are reacted with concentrated hydrochloric acid, followed by isolation of the target product in a known manner.