SU465783A3 - Method for preparing benzenesulfonylurea - Google Patents

Description

Y is a hydrocarbon chain with the number of carbon atoms from 1 to 3, predominantly the –SPg – CHg – Low molecule group of alkyl and 1–4 carbon atoms in the straight or branched chain.

The low molecular weight acyl is an acyl residue with 1 to 4 carbon atoms, with a straight or branched chain.

According to the above definitions, R can be, for example, methyl, ethyl, propyl, butyl, benzyl, p-phenylethyl. Compounds in which R is hydrogen are preferred.

As an example of a grouping that serves to form a bridge, the following can be cited:

-CHA-, -CHN-SNG-, -CHN,

1 SNS

-CH2-CHg-CH-, -CH-CHg-,

, one

CH3 -CH2 - CH-.

I

SNS

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

The phenyl residue indicated in the formula is predominantly unsubstituted. However, it may also be single or multiple substituted with halogen, lower alkyl or lower alkoxy. It may have substituents in the ortho, meta and para positions, with the para position being preferred.

The compounds obtained can be used as biologically active veins.

The literature describes a process for the preparation of benzenesulfonic acids by oxidizing benzenesulfinic acids by known oxidizing agents such as potassium permanganate in inert solvents.

The proposed method consists in the fact that the correspondingly substituted benzenesulfipyl or benzenesulfenyl urea is oxidized by known oxidizing agents such as potassium permanganate in an inert solvent.

The proposed method allows obtaining a new benzenesulfonylurea, which has valuable properties.

Example. N- 4- (P- (2-methoxy-5-chlorobenzamido) -ethyl} -benzenesulfonyl -N- (4,4-dimethylcyclohexyl) -urea.

A, 3.4 g of 4,4-dimethylcyclohexyl urea is dissolved in 30 ml of pyridine. Adding 4- {| 3- (2-methoxy-5-chlorobenzamido) -ethyl} -benzenesulfinylchloride. Derived from 7 g of 4- {P- (2-methoxy-5-chlorobenzamido) -ethyl)

-sulfuric acid and thionyl chloride acid (slight warming occurs). Transparent. after 15 minutes, the solution is introduced into a mixture of ice-water and dilute hydrochloric acid, the blue-light precipitate is filtered off, washed with 1% ammonia. After recrystallization of the precipitate from methanol, N- 4- {p- (2-methoxy-5-chlorobenzamido) -ethyl) -benzenesulfinyl-N (4,4-dimethylcyclohexyl) -urea is obtained; m.p. 135-137 ° C (with decomposition.).

B. 1 g of the urea prepared above is dissolved in dimethylformamide and, when heated, an aqueous solution of potassium permanganate is added in excess.

After filtering off the manganese dioxide, water and dilute hydrochloric acid are added, and the resulting precipitate is not recrystallized from methanol.

N-4-j p- (2-methoxy-5-chlorobenzamido) -ethyl) -benzenesulfopyl-N- (4,4-dimethylcyclohexyl) -urea is obtained; m.p. 177-178 ° C.

Subject invention

The method of producing benzenesulfonylurea of the general formula

X-CO-N-Y-Ar-SOa-NH-CO-NH-R,

I r

or its salts, where - phenyle.

R is a low molecular weight alkyl group, low molecular weight phenylalkyl or preferably hydrogen; R - cyclohexyl, disubstituted by methyl and acloxy groups

1-2 carbon atoms; chlorocycle oghexyl, 4-methylcyclohexenyl; spiro- (5.5) uidepil- (3) formula

-oh

exo-trichloro- (3, 2, 1, O- -octane of the formula

dimethyl or 4,4-diethylcyclohexyl;

X - a: phenyl, having as a substituent Z and Z, and Z and Z may be the same or different;

Z is hydrogen, halogen, low molecular weight

alkyl, alkenyl, alkoxyl, alkenoxy, haloalkoxy, alkoxyalkoxy, phenalkoxy,

phenylalkyl, cycloalkoxy, phenyl, fepoxyl,

pismolecular acyl, benzoyl, trifluoromethyl, oxyl, low molecular weight acyloxy, -CN, -N02-,

2 - hydrogen, halogen, low molecular weight alkyl, alkoxy, alkoxyalkoxy, acyloxy, oxyl;

X - b: in addition, it can mean a naphthyl radical, in this case substituted once or twice by halogen, low molecular weight alkyl, low molecular weight alkoxy or hydroxy group; tetrahydronaphthyl or indanyl radical; a thiophene radical, in this case, a single or double substitution1, lower alkyl, phenylalkyl, alkoxyl, alkoxyalkyl, alkenoxy, feiylalkoxy, aryl, halo; tetramethylene or trimethylthienyl residue;

Y is a hydrocarbon chain with the number of carbon atoms from I to 3, preferably group

-CH2-CH2-, characterized in that a suitably substituted benzenesulfinyl or benzenesulfenyl urea is reacted with oxidizing agents such as potassium permanganate, and the resulting

the product is isolated as a free compound or salt in a known manner. Priority featured:

05/28/66 when X, R, Y and Ar are all the values of the radicals X, R, Y and Ar, and Ri means dimethyl- or 4,4-diethylcyclohexyl;

04.18.67 when RI - all other values.