PL93129B1 - - Google Patents

Description

The subject of the invention is a new method for the preparation of the known 3-pyrrolidinyl- (l-propyl-dithiocarbamic acid) with a fungicidal effect. n-pyrrolidine with carbon disulfide in benzene at 25 ° C. According to the literature data (US Patent No. 2,971,884, column 3/4, example 1), a preparation melting at 147-149 ° C is obtained, the analysis of which does not give satisfactory results. The product cannot be obtained in pure form and therefore the preparation method is not suitable. It has been found that the known 3-pyrrolidinyl- (1) -propyl dithiocarbamic acid of the formula I or 2 is obtained by reactions of 1- (3-aminopropyl) -pyrollidine. of formula 3 with carbon disulfide with good yield and purity only when carrying out the reaction in an aqueous environment at a temperature of -10 ° C to + 50 ° C. It is completely unexpected that the choice of water as a solvent makes it possible to obtain 3-pyrrolidinyl- / l acid N-propyl dithiocarbamate in pure form, m.p. 175 ° C. Thus, this method introduces a significant technical progress, because according to the method known from the literature of the discussed compound (as is clear from US Patent No. 2,971,884) it could not be obtained in pure form. The reactions are illustrated in the diagram shown in the drawing. The starting compounds l- (3-aminopropylpyrrolidine (Beilsteins Handbuch der organischen Chemie H 20, E II b) and carbon disulphide are known compounds. Water is used as a diluent, but the amount of water does not matter much for the efficiency and purity The reactions are carried out at a temperature of -10 ° C to + 50 ° C, preferably 0-30 ° C. The reaction components are preferably entered in a stoichiometric ratio, the order of introducing the reactants is not essential for the course of the reaction. By filtering off the reaction product and recrystallization from water, the compound obtained according to the invention has, according to the literature data, a fungicidal effect. It can be mentioned, for example, by treating Alternaria solani (US Pat. No. 2,971,884, column 7/8). 2 93129 The method according to the invention is illustrated by the following example: Example: A solution of 128 g (1 mol) of 1- (3-aminopropyl) -pyrrolidine in 600 ml of water is added dropwise under cooling at urea 10-15 ° C 76 g (1 mol) of carbon disulfide. The mixture is stirred for 1 hour at room temperature, the crystalline is filtered off with suction, washed with ice water and with methanol and dried. 194 g of 3-pyrrolidinyl- (1) -propyl-dithiocarbamic acid of the formula II with a melting point of 175 DEG C. are obtained, which is 95% of theory. The compound can be recrystallized from water, the melting point (175 ° C decomposed) does not change. Analysis: Calculated: 13.7% N, 31.35% S. Obtained: 13.8% N, 31.30% S Using a standard prepared according to the literature data (US Patent No. 2,971,884, example 1), impurities were found in benzene as a solvent at 1350 and 1390 cnr1 in the infrared spectrum. PL

Claims (2)

Claims 1. A process for the preparation of 3-pyrrolidinyl- (1) -propyl-dithiocarbamic acid of formula 1 or 2 by reacting 1- (3-aminopropyl) -pyrrolidine of formula III with carbon disulfide, characterized in that the reactions are carried out in in the water environment at a temperature of -10 ° C to + 50 ° C. 2. The method according to claim The process of claim 1, wherein the reactions are carried out at 0-30 ° C. S N-Cr ^ -CH ^ CH ^ NH-C-SH WZCfRI H S | N-CH-CH-CH-NH-C-S ^ k / (+) 2 2 2 WZCfR2 N-CH-CH-CH-NH2 FORMULA 3 ^ | -CH2-CH2-CH2-NH2 ^ CS2 H s J I! (-) {J-CHj-CHj-CHj-NH-C Sv; SCHEME OF WORK. Typographer. UP PRL, circulation 120 + 18 Price PLN 10 PL