SU468403A3 - Method for preparing benzenesulfonylurea - Google Patents

Description

3

or halide, tetramethylene or tri ™ methylentenyl residue

The hydrocarbon chain has the number of carbon atoms, mainly the group CH „-CHJ, -, or its salts.

The term low molecular weight / nasty alkyl means a radical having 1-4 carbon atoms in a straight or branched chain. The term “low molecular weight acylG” means an acid residue with the number of carbon atoms.

-CH2 -, - CH2-CH2-, -CH - SShch-SNg-SNg,

sh.

Of these, preferred are those in which the benzene ring is bonded to the urea group by two carbon atoms.

The phenyl residue is predominantly

by nature.

However, it may also be substituted once or several times by halogen, lower alkyl, or lower alkoxy, and may be substituted in the ortho, meta and para positions, and the para position is preferred. Received. compounds can be used as biologically active substances,

In the literature, the reaction of the acylation of amines by acid halides in the presence of bases is known.

The proposed method consists in the fact that in benzenesulfonylurea of the formula

BM-T-Ag-SO 2-№i - SO-G - B

,to

where C, Y, AJ and R have the indicated meanings,

the residue is X-CCU.

The acylation of aminoalkylbenzene sulfate urea can be carried out by carrying out an exchange reaction with an appropriately substituted halide; : Acids, for example, haloanhydride, or by exchanging aminoalkylbenzenesulfonylureas with 2-

methoxybenzoyl chloride followed by the introduction of a halogen atom in benzene

draw benzamvdnoy group. Trust; the product is recovered by known techniques OR is salified by treatment with alkaline agents. The proposed method allows to obtain a new 6eH3Dj: sulfonylurea, possessing valuable properties.

four

Lerode 1-4 in straight or branched chain.,

J may be, for example, methyl, scrap, propyl, butyl, benzyl, P g phenylethyl. Compounds in which F is hydrogen are preferred by verses.

As an example of a grouping that serves to form a bridge, 10 are the following:

Shz

sn.

0 Example 1. N- {4- p- (2-Me

tox 5-chlorbeisamido) ethylbenzenesulfa-

3-methoxy-4-methylcyclohexyl) urea,

8.2 g of O-acetamidoethyl) benzenesulfo-1 (3-methoxy-4-methylg Cyclohexyl) urea (mp 151-153 ° C) is boiled together with a solution of 1.6 g of sodium hydroxide in 30 ml of water within 2 hours Mass dak) t. Cool to ambient temperature, mix with J2O ml of acetone and 1.2 ml of glacial acetic acid, after which 4.1 g 2 methoxy-5-chlorobenzoic chloride are added. After 2 hours of stirring at room temperature, the wasp was sucked off. dock, treated with bicarbonate solution, and then reprecipitated from dilute ammonia and hydrochloric acid. The resulting N-M- - {2-methoxy-5-chlorobenz chmido) ethyl 1-benzol sulfate-N (3-methoxy-4-methylcyclohexyl) urea melts at 179-ISO C after recrystallization from a mixture of methanol and dimethyl formate.

PRI mme R 2. M- {4- - (2-Methoxy 5 chlorobenzamido) ethyl benzenesulfo - N - (4-chlorocyclohexyl) urea.

7.8 g N-Gr- (2- "acetamido) 0 benzenesulfo -N- {4-chloroiclohexyl) m1 chevshsh {so pl. 151-153 ° С) with 1.6 g of notry oxide hydroxide and 30 ml of water boil for 2 hours. Then the reaction mixture is cooled to room temperature, 5 O 2 ml of acetone and 1.2 g of glacial acetic acid are added, 4.1 g of 2-methoxy 5-orbenzoate chloride are added in separate pores and stirred for 1 hour. Sediment sucked off, mixed with a solution of bicarbonate and recrystallized from a mixture of methylnol and dimethyl}) or | ualide I polyurea (2-methoxy-5-chlorobenz lido) ethyl belzolsulfo-N (4-cyclohexyl) urea melts at J.78 -179 ° The subject matter of the invention. The method of obtaining benzenesulfonyl liquif liHifibi is offended by the formulas G-CO-K-T-Ar-802-F-CO-W I 1 where LG - pheny en; f is low molecular weight alkyl, low molecular weight phenylalkyl or predominantly hydrogen; C - cyclohexyl, disubstituted by methyl and alkoxygroup with 1-2 carbon atoms, chlorocyclohexyl, spiro (5.5) undecyl- {3) formulas of exo-tricyclo {3.2, 1.0) octane of formula, OO 2 dnmethyl- or 4 , 4-diethylcyclohexyl, 4-methylcyclohexenyl; : X - phenyl, having as a substituent Z and t ;, tfichim 2. And so on. Can be the same or different} 2, - hydrogen, halogen, low coaxial alkyl, alkenyl, alkoxy, alkenoxy, haloalkoxy, alkoxyalkoxy, feiyl } | 1 coxyl, phenyl-Jai-IL, cycloalkoxy, phenyl, phenoxyl, low molecular weight cellyl acyl, ben zoyl, trifluoromethyl, hydroxy group, low molecular weight C1CLLOXYL, 2 - hydrogen, halo, low molecular alkyl, alkyl, alkoxy silyl, 2 - hydrogen, halo, low molecular alkyl, alkyl, alkoxy silyl, 2 - hydrogen, halo, low molecular alkyl, alkyl, alkoxy silyl, 2 - hydrogen, halo, low molecular alkyl, alkyl, alkoxy silyl, 2 - hydrogen, halo, low molecular alkyl, alkyl, alkoxy silyl, 2 - hydrogen, halogen, low molecular acyl, alkyl, alkoxy silyl, 2 - hydrogen, halogen, low molecular acyl alkyl, alkoxy, low molecular acyl; X - naphthyl, if necessary, substituted once or twice by halogen, low molecular weight p1 th alkyl, low molecular weight alkox or oxygene, tetrahydronaphthyle shp indanyl radical, thienyl moiety, if necessary, once or twice substituted by a fused fuser, a pendant, thiene moiety, if necessary, once or twice substituted with a fused fuser, thiene moiety, if necessary, once or twice substituted with an acyl, fumed alkoxyalkoxy, alkeno / xyl, phenylalkoxy, aryl, halogen, tetramethylene or a three methylenethylene residue; A hydrocarbon chain with the number of carbon atoms is 1-3, the predominantly group is CH - CHI, or its salts, characterized in that the benzenesulfonylurea of the general formula HN-Y-Ar-302-NH-CO-NH-R where 1, U, Ag and KJ have the indicated values, undergo acylation, for example, acid halide, respectively, substitute acidic acid, and the target product is isolated by known methods or converted into salt by treating with the use of schiaxical agents. Priorities on the grounds of: 28.05.66 with Ar - phenylene; R is a low molecular weight apical, low molecular weight phenylalkyl or preferably hydrogen; - dimethyl- or 4,4-diethylcyclohexyl; X is phenyl, having Z and 2 as its mixture, and whether Z HZ are different; Methyl, halo, low molecular alkyl, alkenyl, alkoxy, alkoxy, haloalkoxy, alkoxyalkoxy, phenoxy, phenylalkyl, cycloalkoxy, alkyl, cycloalkoxy, phenyl, low methyl acyl, benzoyl methyl benzoyl, methyl benzoyl, methyl benzoyl, methyl benzoyl, methyl benzoyl, alkyl, alkyl, alkoxy, alkyl hydrogen, halo, neecomolecular, alkoxy, alkoxyalkoxy, acyloxy, hydroxy; X - naphthyl, if necessary. - 1 -;, substituted once or twice by halo, low molecular alkyl, low molecular weight alkoxy or hydroxy group, tetrahydronaphthyl or indanyl radical, thienyl oxygen, if necessary once)} {o or twice substituted by alkyl, phenylalkyl, alkoxylic acid, alkoxylic acid, phenylalkyl, alkoxy, or alkenoxy, enylalkoxy, aryl, halogen, tetramethylene or trimethyleneylenyl residue: Y is a hydrocarbon chain with 1-3 carbon atoms, mainly the group is 18.O4.67 with R is cyclohexyl, disubstituted methyl or al hydroxy

with 1–2 carbon atoms, x orcyctopohexyl, (5.5) undeyl- (3) mules

eight

2.4,

exo-trinicio (3,2,1., o) octac.

-4-methyl-1SHclohexenip.