SU450403A3 - Method for preparing substituted thioureidobenzene - Google Patents

Description

(54) METHOD FOR OBTAINING SUBSTITUTED TIOURAIDEOBENZENE

The invention relates to a process for the preparation of substituted thioureidobenol of the general formula S 0 -NH-C-NH-GO-BI ShB2 where X is hydrogen, chlorine, methyl or nitro, R is alkyl with Cj-C, H "is alkylaminocarbonyl with C-Cp, th-: 4O amyothiocarbonyl, unsubstituted or substituted by alkyl with C — C „, 3,3-dimethyl, 1 o ureidothiocarbonyl or 3,3-dimethylthioreidothiocarbonyl. A known method for producing substituted bis (thioureidobenzene by reacting substituted phenylene diamines with carbonyl-thiocyanates. The proposed method is carried out according to the known analog method, but using 2- (3-alkoxycarbonyl-2-touriidoido) nilins as the starting compounds and the corresponding isocyanates are used as the starting compounds 2- (3-alkoxycarbonyl-2-tnourieido) nilins and the corresponding isocyanates are used as the starting compounds 2- (3-alkoxycarbonyl-2-tnourieido) nilins and the corresponding isocyanates are used. It allows to obtain biologically active compounds with the best properties. The proposed method consists in the fact that the compound of the general formula S about HC-NH-CO-BI where X and R - have the indicated meanings, subject to The reaction can be carried out either in the absence of a solvent or in an organic solvent such as acetone, MeTiuji ethyl ketone, methanol, ethanol, dioxane, benzene or TOiyon.

Note ep 1. 1- {3-n-butypureido) -2- (3-ethoxycarboni. 2-thioureido) benzene 4.5 g (O, 05 mol) n-but alisosilane PTS are gradually added to 7.2 g (OOZ mol) 1. (2-aminophenyl) -3 - ethoxycarbonyl-2-iocarbamide in 60 ml of dry benzene at room temperature and stirring, after which-g reaction mixture KV, r t t under reflux and for 1 , 5 h. The reaction mixture is cooled to room temperature and filtered. The resulting colorless crystals are washed with ethanol and dried.

9 g of crude 1- (3-n-butylureido) -2- (3-ethoxycarbonyl-2-thioureido) benzene crystals are obtained having a decomposition temperature of 182 ° C. The decomposition temperature of the crystals recrystallized from ethanol remains 182 ° C.

Found,%: C 53, OO; H 6.25; N 16.40 S 9.25 C.gH22N

Calculated,%: C 53.2; H 6.51; N16.57; S9.47

Example 2. 1- (3-n-propyl-2-thioureido) -2- (3-ethoxycarbonyl-2-thioureido) benzene. 2.4 g (O, O2 mol) of n-propyl isodianate are gradually added to 5.7 g (O, O2 mol) of 1- (2-aminophenyl) -3-ethoxycarbonyl; 2-thiocarbamide in 30 ml of acetone at room temperature and stirring, and then the reaction mixture is refluxed for 4 hours. The reaction mixture is then cooled to room temperature and poured into water. The resulting oily product remains Formula H — C — N H — C — 0NH — C — I HA

H-C-MNISIH-C-NHN

about

they stay for the night; ex) 6th crystal is washed with 10% hydrochloric acid, then with water and dried.

By recrystallization from an aqueous solution of ethanol, light yellow crystals are obtained, having a decomposition temperature of 132.5-133.5 ° C.

Found,%: C 49.55; H 5.98 ;:: N16.5O

 N40282

Calculated,%: C 49.41; H 5i88; .Nl6j47

Froze l- (3-N, N-Dn-methyl-ocarbamoyl-2-thioureido) -2- (3-methoxycarbonyl-2-thioureido) benzene. 20 ml of an acetone solution containing 7.3 g (0.05 mol) of freshly prepared dimethylthiocarbamoyl isothiocyanate are added dropwise to 11.3 g (O, 05 mol) of 2- (3-methoxycarbonyl-2-thioureido) aniline in 50 ml of acetone at a temperature below 0 ° C, after which the reaction mixture is kept at room temperature for 1 hour with stirring. Then acetone is distilled off from the mixture under reduced pressure and the residue is taken up in water.

Using recrystallization from ethano ' from the residue, 12 g of crystals are obtained having a decomposition temperature of 148-149 ° C .49 ° C.

Found,%: C 41.83; H 4.6 O; N18.85 825.80

Calculated,%: C 41.94; H 4.58;

N18.87; 25.88

 In a similar way, the compounds obtained are presented in Table. one.

T, pl. or T.

The connection {ps

1- {3-n-butylureido) -2- (3-mutoxy182-183 carbonyl l-2-ioureido) benzene CH 5irbonyl-2-thioureido) b | 1- (3-n-propylureido) -2- (3- methoxy1 132,5-133,5

NH-C-O-JQHs

-NH-H-CaHs -Tog

1- (3-n-butypureido) -2- (3-ethoxycarboni l-2-thioureeo) benzo-l

1- (2-thiocarbamoyl-aminopevil) -3-ethoxycarbonylthiocarbamide157 (p)

-Ml-C-CaHsi

.

-NH-C-O-CaHsL

-NH with aliv. N-propyl-2 ioureido) -2- (3-.

 / -ethoxycarbonyl-2-thioureido) -beneol 132-133,5 (p)

1- (3-ethoxycarbonyl-2-thioureido) -

-2- {3-methyl-2-thioureido) benzene 16O-161

j 1- (3- N, N-Methylamino-thiocarboxylic 12-thioureidr) benzene148-149 (p)

NH-C-O-C HB I

NH-C-N H

Sn-2-oypeideo) -2- (Etotoksnkyrbonyl S IH-C-NH-CC-NH-C O

159-16O (p) O-CH "1- {3- (h, N-dimethylaminocarbonyl-2-thioureido) -2- {3-MetOKCHKap6o-2-thioureido) -benzene,

Subject invention

1 i

 The method of obtaining substituted thioureido

benzene of the general formula

1 V

NH-C-NH-C-0-R NHR,

X is hydrogen, chlorine, methyl or nitro

group, R is alkyl with C - C,

R - adkylaminocarbonyl with C.-C, 45

aminothiocarbonyl unsubstituted or substituted by alkyl with C -Ci, 3,3-dimethylureidothiocarbonyl T or 3,3-dimethylthioureothothiocar-j

AT

Bonil, characterized in that the compound of the general formula

I

NH-C-NHNHg

f where X and Rj - have the indicated meanings, 1 is reacted with the corresponding isocyanate or isothiocyanate with i followed by isolation of the target product by known techniques. | Priority by order: I 12. 10, 68 with Р {„- alkylaminocarbo substituted or substituted alkyl with C

18. U1.69 with -, 3-dimethyl and dotiocarbonyl or 3,3-dimethylthioureido thiocarbranyl.