SU403168A1 - Method of producing substituted benzene sulfonylsulfonyl chloride - Google Patents

Description

The invention relates to a process for the preparation of a new kneaded benzenesulfonylurea of the formula S02-No. I-CO-1SR: C CH-CHg, in which the butylurea of the formula NH, —CO — NH — H — C.H. Vso. SOji-sc / 7C a

Y

where X and Y have the above meaning;

n 1 or 2.

In the starting compounds, the term "halogen includes all halogens, especially chlorine and bromine, and the term" lower alkyl includes normal, cyclic and branched chain alkyls containing up to 6 carbon atoms, preferably methyl. In compounds where the phenyl ring is substituted by an alkyl radical, halogen, alkoxyl or hydroxyl, the substituents are in the ortho or meta position, but mainly in the para position of the phenyl ring.

In the compound, where Xi is hydrogen, YI is lower alkyl, halogen, hydroxyl or hydrogen, and when X is methyl or halogen, then Y is hydrogen, lower alkyl or halogen.

The reaction is carried out predominantly in an inert organic solvent at the boiling point.

The resulting compounds can be converted to salts with alkali or alkaline earth metals or ammonia.

Example. 1- (a, a-Methylethoxyphenyl) -3- (p-toluenesulfonyl) -urea.

A solution of 1.9 g of p-toluenesulfonyl chloride in 50 ml of petroleum ether is added to a solution of 1.9 g of 3-hydroxy-1- (a, a-methylethoxyphenyl) -urea in 100 ml of petroleum ether. The mixture is heated under reflux and stirred for 2 hours, cooled and extracted with 2 N NaOH. The aqueous extract is acidified with acetic acid, 1 (a, a-methylethoxyphenyl) -3 - (α-toluenesulfonyl) -urea is precipitated, which is filtered off, washed with water and recrystallized from acetone.

T. pl. 180-181 ° С, (-а) (С 2%, dioxane).

Subject invention

The method of obtaining the substituted benzenesulfonylurea of formula

L N ../ J

 V-SOo-NHrrCO-KiR-CH-CH9-T 1

z rr / I 4,

.-.

or her cojiH,

where X and Xi are hydrogen, methyl, methoxy or

halogen;

Y and YI are hydrogen, lower alkyl, oxygroup, lower alkoxy or halogen;

R is hydrogen or methyl, provided that

a) X and Y do not simultaneously mean hydrogen,

b) if X - / g-chlorine, Y is hydrogen, then at least one of the radicals Xi, YI and R is not hydrogen,

about tl and h and y i and so that urea formula

riaN- СО-Ж1- СН - СНг СН

where R, Xy, YI are as defined above,

subjected to interaction with the acid halide of the formula

XN.-

 .-halide Y

where X and Y are of higher order, followed by isolation of the target product or its translation into salt by known methods.

Priority by featured;

19.HP.1969 for compounds of the formula, in which

X, Xi is hydrogen, methyl or halogen,

Y, Y is hydrogen, lower alkyl, hydroxy, lower alkoxy or halogen,

R is hydrogen or methyl.

13.VIII.1970 for compounds of the formula, in which

X, Xi is methoxy.