SU370203A1 - Method of producing phenyl ethers of aryl (or alkyl) thioalkanesulfonic acids - Google Patents

Description

one

The invention relates to a new process for the preparation of new compounds, the substituted phenyl esters of arnl (or alkyl) thioalkanesulfonic acids of the general formula

RSCHCH, SOaOArX, (1)

I

sn,

where R is aryl, alkyl Ar is aryl

X is an alkyl, alkoxy, halogen, which can be used as biologically active substances in agriculture, as well as additives to plastics.

The method for preparing di- (p-phenylthioethyl) sulfones of the general formula ArSCHaCHaSOzCHsCHaSAr (II), where Ar is aryl, is known through the interaction of thiophenols and divinyl sulfone, which have pesticidal properties.

However, in the literature there are no data on obtaining compounds of General formula I, with valuable physiological properties.

In order to obtain phenyl esters, aryl (or alkyl) thioalkanesulfonic acids, which have pesticidal properties and are valuable additives to plastics, a method for the preparation of compounds of general formula I is proposed.

in the reaction of nucleophilic addition, thiophenols or mercaptans are reacted with phenyl esters of alkene sulfonic acids, for example allyl sulfonic acid, in the presence of an organic base, for example triethylamine, at a temperature of 50-100 ° C.

Example 1. The i-chlorophenyl ester of p-phenylthiopropane sulfonic acid. 2.6 g (0.022 g mol) of thiophenol and 1-2 drops of triethylamine were added to 4.6 g (0.02 g-mol) of ha-chlorophenyl ether of allyl sulfonic acid in 10 ml of benzene. The mixture is heated at 60 ° C.

4 hours, washed with a solution of water, dissolved with MgSO4, distilled off the solvent. In the residue, 6.7 g (98%) of an almost pure product are obtained. T. pl. 70-73 ° C. After recrystallization from the standard, 6.3 g (90%) are obtained.

i-chlorophenyl ester of p-phenylthiopropane sulfonic acid. T. pl. 78-79 ° C. Found, o / o: S 18.64. Calculated,%: S 18.75. PMR spectrum; doublet 6-1.6 ppm - the group SNS;

multiplet 6-3.5 - group multiplet

6-3,65-3,88 - CH group, - phenyl cores

SbNb and SbN4C1 - multiplet 6-7.0-7.5, the ratio of protons is 3: 2: 1: 9.

Example 2. / g-krezplovogo ether

p-phenylthiopropanesulfonic.

3

to 0.02 g-mol of d-cresyl ester of allylsulfonic acid (p 1.5208) in 10 ml of benzene

0.022 g-mol of thiofiol and 1-2 drops of triethylamine are added. The mixture is heated at 70 ° C for 5 hours. The reaction mass is washed with soda solution, water, dried with MgSO4, the solvent is distilled off.

After recrystallization from the standard, β-cresyl ester of p-phenylthiophenesulfonic acid is obtained, yield 85%. T. pl. 64-65.5 ° C.

Found, “/ o: S 20.11.

Calculated,%: S 19.90.

Example: 3. Preparation of p-ethylthiopronanesulfonic acid rt-chlorophenyl ester.

To 0.02 gmol of allyl sulfonic acid chlorophenyl ester (m.p. 4b.degree. C.) in 10 ml of benzene was added 0.025 gmol of ethyl mercaptan and 2-3 capes of triethylamine.

The mixture is heated in an ampoule of 80–90 ° C for 8 h. The target product is isolated in a similar manner.

examples 1 and 2. Output 70%. T. Kip. 109-116 ° / 0.1 mmHg Art., ng 1,5405, df 1.2780, MKD 72.08, calculated MKD 72.64.

The resulting products are colorless liquids or crystalline substances that are stable during storage, soluble in ether, acetone, benzene, insoluble in water and leftholate ether.

Will drive the invention

Claims (2)

1. A process for the preparation of phenyl esters, aryl (or alkyl) thioalkanesulfonic acids, characterized in that thiophenols or mercaptans react with phenyl esters of alkylene sulfonic acids, for example allylsulfonic acid, in the presence of a catalyst at 50-100 ° C, followed by isolation of the desired product by a known method. 2. A method according to claim 1, characterized in that organic bases, such as triethylamine, are used as the catalyst.