SU558910A1 - Method for preparing 3-alk (aryl) hydroxy-2-hydroxypropyl esters of dialkyldithiocarbamic acid - Google Patents

Description

55 3 phenyloxy ethers taken in a molar medium with an organic ratio of 1: 1 to (benzene, alcohol, water; whom alcohol is boiled) at its boiling point. The reaction time is 2-16 hours, the yield of esters is 66-91% of the theoretical one. {. Purification of the target products from side products is performed by chromatographic means. This method is characterized by a long reaction time, the formation of by-products and the complexity of their separation (usually using the chromatographic method for this). In order to simplify the process and increase the yield of the target product, a method is proposed for the preparation of 3-alk (aryl.} N, N-dialkyl dithiocarbamic acid hydroxy-12-hydroxy-propyl esters, the distinctive feature of which is that the process is carried out in the presence of a catalyst, -sodium-alkali, taken in an amount of 0.1-0.5 mol / mol of the starting reagent. The method is carried out as follows. To a solution of sodium dialkyldithiocarbamate and 1-chloro-2-hydroxy-3-propylacyl (phenyl) ovine ether, taken in a molar ratio of 1: 1, in aqueous alcohol to Add 0.5-0.1 mol of caustic soda per 1 mol of the starting reagent. The mixture is stirred for 10-20 minutes at room temperature. The desired product which is separated from the solution is separated by decantation. The analysis of the isolated products by thin layer chromatography indicates to the almost complete absence of by-products. The proposed method allows to shorten the reaction time significantly, to conduct the process without heating with a quantitative yield of the target products of a high degree of pureness, achieved without further purification. In addition, it becomes possible to easily carry out and burst technology. Example 1. To 22.5 g (0.1 mol) of sodium diatildithiocarbamate (hereinafter crystalline hydrate with three molecules of water) add 70 g of aqueous alcohol and 16.7 g (OD mol) of 1-HLOR-2-OXY-3 -propyl butyl ether. In the resulting, after stirring until the starting components are completely dissolved, the reaction mixture is added 2 g (0.05 mol) of sodium hydroxide and stirred for another 5-10 minutes. The reaction mixture is stratified into the desired product and a water-alcohol solution of alkali. The desired product, 3-butoxy-2-hydroxy-propyl ester of N, N-diethyl dithioxy-bamic acid, is separated by decantation, washed until neutral, and dried, the yield is 27.7 g (99% of the theoretical). . Example 2; To a mixture consisting of 22.5 g of sodium diethyl dithiocarbamate and 16.7 g of 1-chloro-2-hydroxy-3-propylbutyl ether is added a water-alcohol solution: alkali, obtained after separating the reaction mass of the previous experiment {see example 1). The resulting mixture is | stirred for 15-20 minutes. The desired product was isolated in the described manner, yield 27.2 g (97.2% of the theoretical). I. .. Example 3. To 11.25 g (0.05 mol / dinethyldithiocarbamate | sodium, add 35 g of an aqueous alcohol and 12.54 g (.0.05 mol) of 1-chloro-2-hydroxy-3-hydroxyldecyl alcohol After dissolving the reagents, 1 g (0.025 mol) of sodium hydroxide is added to the mixture, stirred for 15-2 O min. The desired product 3 N-N-diethyl propyl ester of N, N-diethyl dithiocarbamic acid is isolated in the described manner, yield 17, 9 g (98.1% of theoretical). Example 4. To a solution prepared similarly to that described in Example 1 of 2.25 g (0.01 mol) | sodium diethyldithiocarbamate, 2.5 g (0.6 l mol) 1. -chloro-2-hydroxy-3-propyl-tl - ret-butylphenyl ether and 7 ml of an aqueous alcohol, 0.16 g (0.004 mol): caustic soda is added. After 2O-m; n-minute mixing of the target product — G – P-tert. butylphenoxy-2-hydroxy propyl ether N. -Diethyl-dithiakero-amoic acid was isolated by the method described above, yield 3.33 g (96.3% of theoretical). Example 5. To a solution prepared by the method described from 4.50 g (0, O2 mol) sodium diethyldithiocarbamate, 3.73 g of 1-chloro-2-hydroxy-3-propylphenyl ether and 14 g of an aqueous alcohol; 0.16 g (0.004 mol) of sodium hydroxide are added. OnHcaHHbiM in a way get | 3- (Be-. Noxy-2-hydroxy-propyl ester of N, N-diethyl dithiocarbamic acid, yield 5.85 g (97.5% of the theoretical). Example 6. According to the described procedure from 7 , 0 g (0.025 mol) of sodium dibutyl dithiocarbamate (crystalline hydrate with three water molecules), 3.8 g (0, O25 mol) 1-chloro P-2-OXY-3-propyl propyl ester in 22 g of aqueous alcohol is obtained at addition of 0.48 g (0.012 mol) of sodium hydroxide 3-propoxy-2-hydroxy-propyl ester of N, N-dibutyldithiocarbamic acid, reaction time 15 minutes, yield | 7.86 g (98.0% of the theoretical).

five

Formula 3 and b

regen e

1, Creation of the preparation of 3-alk (aryl) hydroxy-. 2-ox1 (propyl esters of N, N-a of an-1 kildigiocarbamic acid of general formula II to

A) N-0-5-CH, -CH-Ch, -OH

p1 ii 1

5OH

Claims (2)

1 jJ where R is R - alkyl R is alkyl Cj-CD, phenyl, alkyl. / Phenyl, 1b the interaction of sodium salt of dialkyl nitricociocarbamic acid with 1-chloro (-2-hydroxy-3-propylalkl (41enyl) ethers, characterized in that, in order to simplify the process and increase the yield of the target product, the process is carried out in the presence of a sodium alkali catalyst. 2. The method according to claim 1, wherein the sodium alkali is taken in an amount of 0.1-O, 5 mol / mol of the starting reagent.