SU201372A1 - METHOD OF OBTAINING 0-ALKYL-5- (p-ARYLTIOETHYL) - THIOCARBONATES - Google Patents

Description

The present invention relates to a process for the preparation of undescribed compounds of the general formula

ArSCH.CHsSCOOR,

where Ar is a substituted and unsubstituted phenyl;

R is alkyl;

by the interaction of p-arylthioethyl mercaptans with chlorocarbonates in the presence or absence of hydrogen chloride acceptors. The process is carried out with or without organic solvents.

Example 1. O-ethyl-S- (| 3-feiylthioethyl) thiocarbonate.

A. A mixture of 3.4 g (0.02 g-mol) of p-feiylthioethyl mercantane, 2.2 g (0.02 g-mol) of ethyl chloroformate and 10 ml of dry benzene is refluxed for 8 hours. The solvent is distilled off from the reaction mass and the target product is isolated by fractional distillation. 2.5 g (52%) of the substance are obtained; m.p. 152-154 ° C / 2 mm, df 1.1693; p 1.5744; Mrs 68,32, cal. 68.06 (ARs were taken equal to 7.81, as in tolov).

Found,%; S 26.23.

Cutin j oz

while stirring and cooling with ice water, 2.4 g (0.022 g-mol) of ethyl chloroformate and 0.88 g (0.022 g-mol) of sodium hydroxide are added dropwise at the same time as a 20% aqueous solution. The reaction mass is stirred for 2 hours at 20 ° C, washed with water (2 times 10 ml) and dissolved over magnesium sulfate. The final product is isolated by fractional distillation. Yield 86%.

Example 2. 0-ethnl-8-p- (i-thiolylthio) ethyl-thiocarbonate is prepared under the conditions of example 1B from 3.7 g (0.02 g-iolb) | 3- (lg-tolylthio) ethyl mercaptan, 2 , 4 g (0.022 g-lu / gb) ethyl chloroformate, 0.88 g sodium hydroxide. The yield is 78%. T. Kip. 149 150 ° C / 1.2 mm; d. 1.1410,

 1.5670; MRo 73.28; Calc 72.68. Found%: S 24.84.

Ci2Hi8U2S2

Calculated,%: S 25.00.

Example 3. O-ethyl-S-p- (rt-methoxyphenylthio) -ethyl-thiocarbonate is prepared under the conditions of Example 1B from 4 g of p - ("- methoxyphenylthio) ethyl mercaptan, 2.4 g of ethyl chloroformate and 0.88 g of sodium hydroxide . Exit 87%. T. Kip. 163-165 ° C / 1.2 mm; (f ° 1.1927; p 1.5700; MRo 74.82; calc. 74.32.

Found,%: S 23.64. , CiaHiGpaSa

Calculated,%: S 2353.

Example 4. O-ethyl-5-p- (o-methoxyphenylthio) -ethyl-thiocarbonate was prepared under the conditions of Example 1B from 4 g of p- (ortho-methoxyfeiylthio) ethyl mercaptan, 2.4 g of ethyl chloroformate and 0.88 g of sodium hydroxide.

Yield 90%. T. cues. 169 172 ° С / 1.2 лn; &1.1976; p 1.5725; MRg 74.80; Calc 74.32.

Naidio,%: S 23.69.

CiaHieOgSa

Calculated,%: S 23,53.

Example 5. O-ethyl-S-p (, and-chlorophenylthio) ethyl 1-thiocarbonate is prepared under the conditions of Example 1B from 4.1 g of p - (./ and chlorferethio) -ethyl mercaptan, 2.4 g of ethyl chloromate, 0, 88 g sodium hydroxide. Yield 81%. T. Kip. 163-

1.2550; 1.5780; MRg

d

164 ° C / 1.5 li /, 73, 20; Calc 72.83.

S 23.00; C1 12.90.

Found, o / o: Vychisleio,,: S 23,14; C1 12.83.

Subject invention

Claims (3)

1. A method of producing 0-alkyl-8- (p-arylthioethyl) tcarbonates of the general formula ArSCHaCHaSCOOR, where Ar is the substituted and the most substitute feiil; R is alkyl, characterized in that rarylgioethyl mercaptans are subjected to interaction with chlorocarbonates. 2. A method according to claim 1, characterized in that the process is carried out in the presence of hydrogen chloride acceptors. 3. A process according to claim 1 and 2, characterized in that the process is carried out in organic solvents.