SU979345A1 - Process for producing 2-benzthiazole sulfene amides - Google Patents

Description

The invention relates to a method for producing 2-benzthiazole sulfenamides of the general formula

di where R is a morpholino or cyclohexylamino radical, 10 which are effective accelerators of rubber vulcanization.

A known method for producing 2-benz'thiazole sulfenamides, which consists in the fact that 2-mercaptobenethia. in the presence of a free corresponding 2θ corresponding amine and an anhydrous inorganic base, the organic layer is separated, washed with hot water and distilled off in vacuo .. Yield 9498%, content of the main product

96% [1J. ²⁵

The disadvantages of this method is the use of anhydrous reagents, the difficulty of isolating the target product, associated with the need _ distillation of organic plants.

vitorite, insufficiently high quality of the target product.

The closest in technical essence and the achieved effect is a method for producing 2-benzthiazolsulfenmorpholide, which consists in the fact that an aqueous solution of the sodium salt of 2-mercaptobenethiaeol is reacted with N-chloromorpholine in an environment of a water-immiscible organic solvent, for example carbon tetrachloride, in the presence of morpholine , the organic layer was separated, washed with water, and distilled off in vacuo. The yield of the target product 99%, so pl. 84-85 ° C [2].

The disadvantages of this method are the use of toxic organic solvent, the difficulty of isolating the target product associated with the need for distillation of the organic solvent and the insufficiently high quality of the target product.

The purpose of the invention is improving the quality of the target product and simplifying the process technology.

The goal is achieved according to the method for producing compounds of general formula I, which consists in the fact that an aqueous solution of the sodium salt of 2-mercapto3 benethiaeone is reacted with chloramine of the general formula

Cl - R, (II) where R has the indicated values, 5 in isopropyl alcohol at 20-60 ° C, and the target product is isolated by diluting the reaction mass with water at a volume ratio of water: isopropyl alcohol equal to 1: 1, respectively , and filter.

The proposed method allows to obtain the target product of high quality with a yield of up to 98%.

Example · 1. ... Preparation of N-oxa-15 diethylenebenz thiazolyl-2-sulfenamide

A flask with a capacity of 250 megapixels, equipped with two electrodes (platinum and silver chloride), a thermometer and a stirrer, was charged with 22.7 g (¢) -, 12 g / mol) of 2-MBT sodium salt in 32.3 ml of water, 16 g (0.17 g / mol) morpholine and 37 ml of isopropyl alcohol. The mixture is heated to 45 ° C and 19.8 g (0.16 g / mol) of chloroform-25 folin in 23 G4L of isopropyl alcohol are added at this temperature for 30 minutes. The end of the reactions is determined by the jump in the redox potential. Then the reaction mass is cooled to 20 ° C, 60 ml of water are added for 15 20 minutes at 20-25 ° C. At this temperature, give an exposure of 30-40 minutes, after which the product is filtered off, washed. A filtrate containing 16 g (0.18 g / mol) of morpholine was used 35 to produce chloramine in the following synthesis. 29 g of sulfenamide M are obtained. 96% yield. The content of the main substance is 97%. Mp 84-85 ° C.

PRI me R 2. Obtaining N-oxa-40 diethylbenzothiazolyl-2-sulfenamide.

Getting chloromorpholine. In a 250 ml flask equipped with two electrodes, a thermometer and a stirrer, 74 ml of sodium hypochlorite 45 (active chlorine content 180 g / L) are charged, cooled to 5 ° C and the filtrate obtained from the previous synthesis is added over 30 minutes. The end of the reaction is determined by the jump in the oxidation-reduction jq potential. The solution is stratified into two layers, the top layer in an amount of 40 ml, containing 19.8 g (0.16 g / mol) of chloromorpholine and 23 ml of isopropyl alcohol, is sent ** to receive sulpheamide M. The lower water-alcohol layer is sent to regenerate isopropyl alcohol.

Obtaining sulfenamide M is carried out analogously to example 1.

Example 3. Obtaining N-cyclohexylbenzothiazolyl-2-sulfenamide.

In a flask equipped as in Example 1, 22.7 g (0.12 g / mol) of 2-MBT sodium salt in 32.3 ml of water, 17.9 (0.18 g / mol) of cyclohexylamine, 30 ml of isopropyl are charged alcohol. At 30-50 ° C, 21.5 g (0.16 g / mol) of a solution of chlorocyclohexylamine in 30 ml of isopropyl alcohol are added over a period of 10-15 minutes. Then the reaction mass is cooled, the product is isolated by adding 50 ml of water, sold and filtered. The filtrate is stratified into two layers. A top layer containing 60 ml of isopropyl alcohol and 17.9 g (0.18 g / mol) of cyclohexylamine was used to produce chloramine (Example 2). Obtain 31 g of sulfenamide C, which is 98% of the output, counting on the original 2-MBT. The content of the main product is 98%. Mp 100 101 ° C.

Claims (1)

Claim A method of obtaining 2-benzothiazole sulfenamides of the general formula where R is a morpholino or cyclohexyl amino radical by reacting an aqueous solution of the sodium salt of 2-mercaptobenzthiazole with chloramine at an elevated temperature in an organic solvent, characterized in that, in order to improve the quality of the target product and simplify the process technology use chloramine of the general formula Cl - R, where R has the indicated meanings, the process is carried out in isopropyl alcohol and the target product is isolated by diluting the reaction mass with water at a volume ratio of water to isopropyl alcohol of 1: 1.