SU1384587A1 - Method of producing 2-seleno-5-arylidentiazolidine-4-ons and method of producing 2-selenothiazolidine-4-on - Google Patents

Abstract

The invention relates to heterocyclic compounds, in particular to the preparation of 2-seleno-5-arylidene giazolidin-4-BOTH of the formula I R -. SI "С С (0) - NH-C (Se) -, where R is free phenyl, monosubstituted with methoxy or oxy group phenyl, mp or disubstituted with halogen atom phenyl, 2-hydroxy-5-nitrophenyl or 5-nitrofurnl2 and 2-selenothiazolidine-4-one (I) o. The goal is to simplify the process, increase the yield, expand the range of target compounds and develop a method for producing a new intermediate in their synthesis. Getting connections

Description

The invention relates to organic chemistry, specifically to an improved method for producing 2-seleno-5-arylidenethiazolidin-4-ones and to a new method for producing a new intermediate in their synthesis 2-selenothiazolidin-4-one, 2-seleno-5- Arsh1Identiazolidin-4 they can be used to obtain biologically active compounds, as well as to obtain dyes

The purpose of the invention is to simplify the process, increase the yield and expand the range of 2-seleno-5-arylidentia-ZOLIDIN-4-ONOV and create a new method for producing a new intermediate in their synthesis.

The goal is achieved by subjecting rhodopacetic acid ester

interaction with a solution of hydrogen selenide in a dry dioxane medium with heating, preferably at 70–80 ° C, and the resulting intermediate new product 2-selenoothiazolidin-4- is then reacted with an aromatic aldehyde at boiling in a glacial acetic acid.

The invention is illustrated by the following examples of

Example. Preparation of 2-seleniazolidin-4-o. 14.5 g (0.1 mol) of rhodanoacetic acid ethyl ester in 30 MP of dry dioxane are added to a solution containing 12.4 g (0.15 mol) of hydrogen selenide in 100 ml of dry dioxane previously prepared by saturating dioxane with hydrogen selenide at 0 ° C. The mixture is heated at 70-80 ° C for 1 h, then a small amount of elemental selenium that has been filtered is filtered off and the solvent is distilled off in vacuum by 2/3 volume o The crystalline mass that is recrystallized from ethyl acetate-hexane ; 3 and get bright yellow prismatic blue crystals with t.sht. 170-171 ° C.

The yield of 18.2 g (96%).

Found,%: N 7.43; S 17.50; Se 44.23.

C, H ,, NOSSe

Calculated,%: N 7.78 Se 43.83j

S 17.78;

Example 2. Preparation of 2-seleno-5 (o-chlorobenzylidene) thiazolidin-4-one.

1.8 g (.0.01 mol) of 2-seleno-thiazolidin-4-one and 1.41 g (0.01 mol) of o-chloro-bananesaldehyde are boiled in 15 ml of glacial acetic acid for 10 minutes. Upon completion of the heating, the mixture crystallizes into a mass of shiny red needles. It is filtered and recrystallized from acetone with water (1: 3). Light brown light needles with TopPo 201-202 ° C are obtained. Yield 2.9 g (98%).

Found,%: N 4.15; S 10.09; Se 26.70o

C, ONBS1Y088e

Calculated,%: N 4.63; S 10.59; Se 26.09 ..

Similarly, other 2-villages of no-5-arylidentiazolidin-4-onyo Constants are obtained, the yield and physicochemical data are given in the table.

The proposed method allows to simplify the process of obtaining 2-seleno-5-arylidentiazolid-4-ones by reducing the number of stages and to obtain the desired products in high yield.

Claims (1)

Invention Formula 1. The method for preparing 2-seleno-5-arylidene-thiazolidin-4-ones of the general formula (1 R-, A8e about where R is free phenyl, monosubstituted by a methoxy or hydroxy group, phenyl, Mn- or disubstituted by a halogen atom, phenyl, 7 2-hydroxy-5-nitrophenyl or 5-nitrofuryl-2, using the interaction of 2,4-diketothiazolidine with aromatic aldehyde when heated in glacial acetic acid, characterized in that, in order to simplify the process, increase the yield and expand the range of target products, the ester of rhd acetic acid of the general formula (II) NCS-CH -Cf 1 ORi where R, is lower alkyl, is reacted with a solution of hydrogen selenide in a dry dioxane environment with heating and the resulting 2-selenothiazolidin-4 is of the general formula (III) ABOUT TSIH Tgl Se subjected to interaction with aromatic aldehyde of General formula (IV) R - CHO ,, where R has the indicated meanings, when boiling in glacial acetic acid, 2о The method according to claim 1, 1, and 2, and t. rhodanoacetic acid ester and hydrogen selenide are carried out at 70- BO C. The method for producing 2-selenothiazolidin-4-one of formula (III), characterized in that the ester of rhodioacetic acid of general formula (II) is reacted with a solution of hydrogen selenide in a dry dioxane environment by heating o 4. The method according to p. 3, o tl and h and the fact that the interaction of the ester of rhdanoacetic acid and hydrogen selenide is carried out at 70–80 Co NH note. Compounds 5 and 9 crystallize from a mixture of acetone - water 1; 3, the rest of dimethylsulfox.