SU453831A3 - METHOD OF OBTAINING SUBSTITUTED TIOURAIDOBENZENE - Google Patents

Description

one

This invention relates to a process for the preparation of new substituted thioureidobenzene of the general formula

H-CS-KH-COORi

where X is hydrogen, chlorine, methyl or nitro,

RI is alkyl with Ci-4; R2 is hydrogen or methyl, is hydrogen, methyl, formyl, alkylcarbonyl with C2-C3,

cyclopropylcarbonyl, benzoyl; alkyloxycarbonyl with Cz-C3, alkylaminocarbonyl with 04-GS, thioformyl; unsubstituted or substituted with Ci-C3 alkyl, aminothiocarbonyl, 3,3-dimethylureidothiocarbonyl or 3,3-dimethylthioureidothiocarbonyl;

d - inorganic or organic acid.

A method of producing amine salts by reacting organic or inorganic acids with amines is known. The proposed method is based on the well-known chemical method. However, the use of new substituted thioureidobenzene as starting compounds allows the preparation of biologically active compounds with improved properties.

The proposed method is that the compound of the formula

, Ж-С8-М1-СООБ, Ra

where X, RI-Cs have the indicated meanings, are reacted with an acid. The reaction is carried out in an inert organic solvent, for example acetone, dioxane, methanol or ethanol, at room temperature.

Example. 2- (3-Ethoxycarbonyl-2-thioureido) -aniline chloride (compound 3)

1 ml of concentrated PS1 is gradually added at room temperature with stirring to a solution of 2.4 g of 2- (3-ethoxycarbonyl-2-thioureido) -aniline in 25 ml of ocean d3. The mixture is kept for 30 minutes, evaporated in a dioxan vacuum, the residue is washed with acetone and 2.5 g of crystals are obtained with m. 188 ° C. Found,%: C 43.60; H 5.12; N 15.20; 5 S 11.45.

Compound Formula

Temperature

Chemical name of decomposition, ° С 4 СюНмСШзОЗЗ. Calculated,%: C 43.56; H 5.08; N 15.25; S 11.62. Compounds corresponding to formula I and obtained by the proposed method are presented in Table. one.

CH,

2- (3-Methoxycarbonyl-2-thioureido) -aniline nitrate

0-CH3

2- (3-Methoxycarbonyl-2-thioureido) -anilinoxalate —C., H5

2- (3-Ethoxycarbonyl-2-thioureido) -aniline chloride

With „H.j

2- (3-Ethoxycarbonyl-2-thioureido) -aniline nitrate

, H5

2- (3-Ethoxncarbonyl-2-thioureido) -anilinoxalate

1Г-ЬГг1-С-Ь1Н-С- 0-С-Л5

2- (3-Ethoxycarbonyl-2-thioureido) -aniline-l80zN toluensulfonate

from oz

2- (3-Ethoxycarbonyl-2-thioureido) -K, M-dimethylamidine-chloride

Subject invention

The method of obtaining substituted thioureidobenzene of the general formula

, ТЧН-С8-Ш-СООВ1

153

151.5-152

188

140.2-140.3

140

174

167-168

where X is hydrogen, chlorine, methyl or nitro,

RI is alkyl with Ci-C4, is hydrogen or methyl,

Cs - hydrogen, methyl, formyl, alkylcarbonyl with C2-C3,

benzoyl, cyclopropylcarbonyl; C 2 -C 3 alkyloxycarbonyl, C 4 -C 5 alkylaminocarbonyl, thioformyl; unsubstituted or substituted with Ci-C3 alkyl, aminothiocarbonyl, 3,3-dimethylureidothiocarbonyl or 3,3-dimethylthioureidothiocarbopyl; 5 A is an inorganic or organic acid, characterized in that the compound of the formula .oOR, NH Lb gcp v-vjvjn, where X, RI-Ra have the indicated values, 5 10 6 is reacted with an acid and the target product is isolated in a known manner Priority on the signs: 11/18/68 with RI - alkyl with R2, Cs is hydrogen. 09.12.68 with R2, Rs - methyl. 06/18/69 with Rs - formyl, alkylcarbonyl with C2-C3, benzoyl, cyclopropylcarbonyl, alkoxycarbonyl with 2-Cz, alkylaminocarboNIL with C4-GS, thioformyl, unsubstituted or substituted by alkyl with Ci-Cz aminothiocarbonyl, 3,3-dimethylureidohydro-iridocarbonyl, , 3-dimethylthioureidothiocarbonyl.