SU1201283A1 - Method of producing 2-cyclohexylthio-1,3-oxathiolan - Google Patents

Abstract

1. A process for the preparation of 2-cyclohexylthio-1, 3-oxathiolane, characterized in that diethoxycyclohexylthiomethane is reacted with mercaptoethanol in the presence of an acid catalyst with heating. 2. The method according to claim 1, which is distinguished by the fact that the process is carried out at 78-80 s. , 3. The method according to claim 1, about t l and h a - y y and with the fact that sulfonic cation exchanger KU-2 is used as an acid catalyst. . . (L with

Description

00 The invention relates to organic chemistry, namely to a new process for the preparation of a new derivative of 1,3-oxathiolane-2 cyclohexclthio-1, 3-oxathiolane, which can be used in the synthesis of biologically active substances. The purpose of the invention is to obtain a derivative of 1,3-oxathiolane, which can be used in the synthesis of biologically active substances. The following are examples of the synthesis of the starting and target products. Example 1. Stage. A mole flask was charged with 1 mol (148 g) of triethoxymethane, 1 mol (116 g) of cyclohexylmercaptan, and 10 sulfonic cation exchanger KU-2. The reaction mixture is heated to and 2 mol (92 g) of ethanol are distilled off. The residue is subjected to vacuum distillation. The yield of 95% of diethoxycyclohexylthiomethane on the reacted triethoxymethane (207 g), T.kip. mm Hg a; р ° 1.4746. 2 stage. In a round bottom flask, one mole (218 g) of three was charged: ethoxy. Cyclohexylthiomethane, 1 mole (78 g) of mercaptoethanol, and 10 g, heated to 78 ° C, and 2 mol (92 g) of ethanol were distilled off. The residue is subjected to vacuum distillation. The output of 2-cyclohexylthio-I, 3-oxathiolane 90% (184 g) on the reacted mercaptoethanol. T. Kip. 114s / 2 mm Hg Pr 1.4715. PMR spectrum (CCIi, ppm from GCSS): 1.0-2.1 m (II n, c CgH,), 2.5-3.0 m (2H, -CHj-), 4.0 -4.33 m (2H, -CHN-O-), 6.33 s (1H, CH). Example 2. The first stage is carried out as described in Example 1. Stage 2. 1.1 mol (239.8 g) of dietic sicylohexylthiomethane, 1.1 mol (85.8 g) of mercaptoethanol and 10 g of KU-2 are loaded into a round bottom flask. 2.2 mol (101 g) of ethanol is heated to and distilled out. The residue is subjected to vacuum distillation. The yield of 2-cyclohexylthio-1,3-oxathiolane 91% (.186 g) on the reacted mercaptoethanol. The physicochemical constants are similar to those specified in Example 1. Example 3. The first stage is carried out as described in Example 1. Stage 2. 1.2 mol (216 g) of dieto832 of cyclohexylthiomethane, 1.2 mol (93.6 g) of mercaptoethanol, and 10 g of KU-2 are loaded into a round bottom flask. The reaction mixture is heated to 80 ° C and 2.4 mol (110 g) of ethanol is distilled off. The residue is subjected to vacuum distillation. The yield of 2-cyclohexylthio-1, 3-oxathiolane 92% (118 g) on the reacted mercaptoethanol. The physicochemical constants are similar to those specified in Example 1. Example 4. Step 1 is carried out as described in Example 1. 2 stage. Diethoxycyclohexylthiomethane 0.9 mol (196 g), 0.9 mol (70.2 g) of mercaptoethanol and 10 g of KU-2 are heated to 77 ° C. Yield 85% (173 g) of the desired product. Example 5. The first stage is carried out as described in Example 1. 2 stage. Diethoxycyclohexylthio-methane 1.3 mol (283 g), mercaptoethanol 1.3 mol (101 g) and 10 g KU-2 are heated to 82 C. The yield is 82% (167 g) of the desired product. Example 6. The first stage is carried out as described in Example 1. Stage 2. 1.0 mol (218 g) of diethoxycyclohexylthiomethane, 1, 0 mol (78 g) of mercaptoethanol, and 10 g of KU-2 are loaded into a round bottom flask, heated to 78 ° C, and the calculated amount of ethanol is distilled off. The residue is subjected to vacuum distillation. The yield of the target product is 90% on the reacted mercaptoethanol. Example 7. The first stage is similar to that shown in example 1. 2 stage. Similar to example 1, but the molar ratio of diethoxycyclohexylthiomethane and mercaptoethanol is 1: 1.1. The yield of the target product is 92%. Example 8. The first stage is similar to that shown in example 1.. 2 stage. Similar to example 1, but the molar ratio of the reactants is 1: 1.2. Yield 91% for reacted mercaptoethanol. Example 9.1 stage is similar to example 1. 2 stage. Similar to example 1, but the molar ratio of the reactants is 1: 0.9 (diethoxycyclohexylthiomethane: mercaptoethanol). The yield of the desired product is 84%.

3 12012834

Example 10. Stage 1. The analysis of sulfuric acid yields a target effect of Example I. Its product is 84% (reaction temperature. Stage. Similar to Example 1, eq., The molar ratio is the molar ratio of the reactants: ethoxycyclohexylthiomethane and mer-

1: 1.3. The yield of the target product is 85% .j of captoethanol 1: 1).

The type of catalyst plays a substantial role. In the case of using the p-toluene role in increasing the yield of sulfonic acid, the yield of the target is

target product. In case of use, 86%.

Claims (1)

1. METHOD FOR PRODUCING 2-CYCLOHEXYLTI0-1.3-0XATI0LANA, characterized in that diethoxycyclohexylthiomethane is reacted with mercaptoethanol in the presence of an acid catalyst upon heating. 2. Way under item 1, about t l and h a - y u and at 78 th with i 1-80 ° C. by what process lead 3. Way by item • 1, about t l and h a - Yu u and S C Z by what in quality acid catalyst use sulfonic cation exchanger KU-2 ... KZ CO> eleven