SU437277A1 - Method for preparing substituted benzosulfonylurea - Google Patents

Description

one

A method is proposed for the preparation of novel substituted benzenesulfonylurea or its salts, which can be used as biologically active compounds.

A known method for producing substituted benzenesulfonylurea by reacting benzenesulfinic acid or its salts, or benzenesulfinic acid anhydride with hydroxyurea.

To obtain new compounds with better properties than the known ones, a method is proposed for the preparation of substituted benzenesulfonic urea of the general formula

f-CO-NH-Y- / S02-NH-40-J "HB

where R is 4.7 - endomethylene perhydroindan-5yl, which can be substituted in position 6 with chlorine, 4,7-endomethylene perhydroindan2-yl, 2,6-endomethylencycloheptyl, 4,4-dimethyl - D2 - cyclohexenyl, D - cyclopentenyl, A - cycloheptenyl, D-cyclooctyl, norkaran7-yl, bicyclo- (5,1,0) -octyl-8, bicyclo- (6,1,0) nonyl-9, bicyclo- (4,2,0) -octyl-7 , 2,5-endocyclobutylene- (1,2) -cyclohexyl, methylcyclopentyl, 3,3-dimethylcyclopentyl, 3-ethylcyclophen2

Tyl, 3-treg-butylcyclopentyl, 2-chlorocyclopentyl, D2-cyclopentenylmethyl, bicyclo- (2, L 1) -hexyl-2, spiro- (2-cyclopropane-pentyl), spiro- (2-cyclobutane-pentyl), spiro (2 -cyclopentane), cyclopropyl, cyclobutyl, 5methyl-D-cyclohexenyl, bicyclo- (3,1,0) -hexyl;

X is phenyl, having the same or different Z and Z as a substituent;

Z is hydrogen, halo, lower alkyl, alkoxy, alkenoxy, alkoxyalkoxy, phenalkoxy, lower acyl, benzoyl, trifluoromethyl, hydroxy; Z is cyan or nitro, hydrogen, halogen, lower alkyl, alkoxy, alkoxyalkoxy, hydroxy;

X is a thiophenic radical, which may, if necessary, be substituted once or twice by lower alkyl, alkoxy, alkoxyalkoxy, alkenoxy, phenalkoxy or halo;

Ivjiij) ct GT

-CH (CH3) -CH, -.

Under lower alkyl in this case should be understood alkyl with the number of carbon atoms 1-4 in the unbranched or branched chain. Lower acyl means acyl containing up to 4 carbon atoms in a branched nly, preferably unbranched chain.

OESNoS (c.) - P.

As a link in this formula, for example, the following ring systems may be mentioned:

OSNOSMoOSNG, OSNz

R

OCli.jCHoOClIj,

CHgO

smallpox,

The proposed method consists in the fact that sootvetstvuyushaya, ue substituted benzenesulfinic acid or alkali salts thereof in nrisutstvii acidic condensing agents or corresponding substituted galoidpronzvodnye (halides) benzenesulfinic acid is reacted with hydroxyurea, in which the NH2 grunpa substituted with R, wherein R is as defined above.

It is advisable to carry out the reaction between sulfinic acids or sulfinic chlorides and hydroxylurea in indifferent solvents, if sulfinic acids or their alkaline salts are used as starting materials, then in this case it is necessary to use acidic condensing agents, for example, thionyl chloride, polyphosphoric acids, anhydrous phosphoric acid or sulfuric acid.

The resulting compounds can be converted to their salts by treating with alkaline agents such as alkali or alkaline earth metal hydroxides, carbonates or bicarbonates of these metals.

Example. N- {4- p- (2-M.eTOKCH-5-chlorobenzamido) ethyl benzenesulfonyl} - N- (3-methylcyclopentyl) urea.

7.1 g of (2-methoxy-5-chlorobenzamido) ethyl benzenesulfinic acid and 3 g of N- (3-methylcyclopentyl) -N-hydroxyurea are suspended in 60 ml of dioxane. To the reaction mixture, 2 ml of thionyl chloride in 20 ml of dioxane is added dropwise, the mixture is heated to 60 ° C for 2 hours, cooled and displaced with water. The precipitate thus obtained is suction filtered and dissolved in 1% ammonia. The solution is filtered and the product which is precipitated after acidification is recrystallized from methanol. Get N- {4- P- (2-methoxy-5-chlorobenamido) ethyl benzenesulfonyl} - iN- (3-methylcyclopentyl) urea with so pl. 156-158 ° C.

Subject invention

The method of obtaining substituted benzenesulfonylurea of the general formula

SOj-NH-CO-NHR

K-CO-NH-Y where R is 4.7-endomethylene perhydroindan 5-yl, which in the b position is chlorine as a substituent, 4,7-endomethylene N perhydroindan-2-yl, 2,6-endomethylencycloheptyl, 4,4-dimethyl -A2-cyclohexenyl, A-cyclopentenyl, A-cyclogeitenyl, A-cyclooctyl, norkaran-7-yl, bicyclo- (5,1,0) - octyl-8, bicyclo- (6,1,0) -nonyl-9 , bicyclo- (4,2,0) -octyl-7, 2,5-endocyclobutylene- (1,2) - cyclohexyl, methylcyclopentyl, 3,3-dimethylcyclopentyl, 3-ethylcyclopentyl, 3-gret-butylcyclopentyl, -2-chlorocyclopentel, A - cyclopentenylmethyl, bicyclo- (2,1,1) -hexyl-2, spiro - (2 - cyclopropanpentyl), spiro- (2-cyclobutane), spiro- (2-cyclopentane-pentyl), cyclopropyl, cyclobutyl, b-methyl-A-cyclohexenyl, bicyclo (3,1,0) -hexyl;

X is phenyl, having the same or different Z and Z as a substituent;

Z is hydrogen, halo, lower alkyl, alkoxy, alkenoxy, alkoxyalkoxy, phenalkoxy, lower acyl, benzoyl, trifluoromethyl, hydroxy;

Z is cyan or nitro, hydrogen, halogen, lower alkyl, alkoxy, alkoxyalkoxy, hydroxy;

X is a thiophene radical which can be substituted once or twice by a lower alkyl, alkoxy, alkoxyalkoxy, alkenoxy, fsnalkoxygroup or halogen; V gh nGH THfTHt - (-Ha - Pa-, - - (M (, (Hj; -, - CH (CH,) - CHj-, characterized in that the corresponding substituted benzenesulfinic acids 6 or their alkaline salts in the presence of acidic condensing agents or corresponding substituted halogen derivatives of benzenesulfinic ACID are reacted with R-substituted hydroxyureas, where R has the indicated meanings, followed by isolation of the desired product or its translation into salt using known techniques.