SU1549955A1 - Method of obtaining mercyry complexes of n-phosphorylated thioamides - Google Patents

Abstract

This invention relates to the chemistry of organoelement compounds, in particular, to methods for producing mercury complexes. N-phosphorylated thioamides of the formula, @ where R is CH ₃ , C ₆ H ₅

X-oxygen, sulfur, which are used in medicine as antiviral drugs or as lubricating oil additives. The goal is to simplify the process, increase the yield and expand the range of target products. The process is carried out by reacting the corresponding N-diisopropoxyphosphoryl (thiophosphoryl) amide with mercury oxide at a molar ratio of 1: (0.75-3), boiling in CCI ₄ or benzene. These conditions allow to increase the yield of the target product from 54 to 92-96% and carry out the process in one stage of the available substances.

Description

The invention relates to an improved process for the preparation of mercury complexes of N-phosphorylated thioamides of the general formula

(о-с3н7-изо) 2

 X /

L x s

II I

(U30-C3H7-0)

where R is CH3, C6H5; X - O, S ,, which can be used in medicine

as antiviral drugs, in agriculture, as additives to lubricating oils.

The purpose of the invention is to simplify the process, increase the yield of target products and expand their range.

PRI me R 1. Mercury complex of N-diisopropoxythiophosphorylthiobenzamide (1a).

A mixture consisting of 2.44 g (0.0077 mol) of N-diisopropoxythiophosphorylthiobenzamide, 1, 67 g (0.0077 mol) of red mercuric oxide, 7 g of anhydrous magnesium sulfate and 60 ml of tetrachloride

SL SL

carbon is boiled under stirring for 1 h. The reaction mass is cooled, filtered, the solvent is removed in vacuo, the residue is recrystallized from hexane. Obtain 3.1 g (96.7%) of light green crystals with so pl. 101-102 ° C. 8 R 52 м.ц. ,

Found,%: C 37.38; H 4.68; R 7.30.

C76H3BHgNau PtS4.

Calculated,%: C 37.48; H 4.56; R 7.44.

IR spectrum, 3,: 630 (); 985 (DEW); 1495 (S-ON-).

EXAMPLE 2 Differs from Example 1 in that a mixture of 3.17 g (0.01 mol) of M-diisopropoxy-phosphoryl thiobenzamide, 6.51 g (0.03 mol) of yellow mercuric oxide in 70 m of carbon tetrachloride, boil for 1 h. Output 3.9 g (94%).

EXAMPLE 3: Differs from example 2 in that a mixture of 3.17 g (0.01 mol) of N-diisopropoxy-phosphoryl thiobenzamide, 2.17 g (0.01 mol) of yellow mercuric oxide and 70 ml of carbon tetrachloride are boiled for 1 hour. The yield is 3.92 g (94.1%).

II p. Example 4. Differs from example 2 in that a mixture consisting of 3.17 g (0.01 mol) of N-diisopropoxy-phosphoryl thiobenzamide, 1.085 g (0.005 mol) of red mercuric oxide and 70 ml carbon tetrachloride,

boil for 1 h. The yield is 3.37 g (81%).

EXAMPLE 5 Differs from Example 2 in that a mixture consisting of 3.17 g (0.01 mol) of N-diisopropoxy-thiophosphoryl thiobenzamide, 2.17 g

(0.01 mol) of red oxide of mercury and 70 ml of benzene, boil with a Dean-Stark trap for 2 hours. Yield 490 g (96%).

EXAMPLE 6 Differs from example 2 in that a mixture consisting of 3.17 g (0.01 mol) of M-diisopropoxy-thiophosphoryl thiobenzamide, 2 s17 g (0.01 mol) of red mercuric oxide and 60 ml of carbon tetrachloride,

boil for 0.5 h. Output 2.5 g (60%).

Example. Mercury complex of N-diisopropoxythiophosphorylthioacetam and (16).

A mixture consisting of 2.55 g (0.01 mol) of N-diisopropoxythiophosphorylthioacetamide, 6.51 g (0.03 mol) of yellow mercuric oxide in 70 ml of carbon tetrachloride, is boiled for 1 h.

,,

with

ten

15

l20

25

zo

Q

Q

-

55

reflux condenser. The reaction mass is filtered, the filtrate is evaporated, the crystals are separated, washed with a small amount of hexane. 3.3 g (93%) of the substance was isolated. M.p. 85-86 ° C; 8 31P 50 ppm

Found,%; C 26S92; H 4.68; P 8.61.

, 4HgNt04F4S4.

Calculated,% C 27.08; H 4.79; R 8.74.

No.C spectrum,}, cm (: 620 (); 990, 1000 (DEW); 1565 ().

II p. And measure 8. Mercury complex of N-diisopropoxyphosphorylthiobenzamide (1c).

A mixture consisting of 3.01 g (0.01 mol) of N-diisopropoxyphosphoryl-thiobenzamide, 4.34 g (0.02 mol) of yellow mercuric oxide and 70 ml of carbon tetrachloride is heated under reflux for 1 hour. The reaction the mass is filtered, evaporated, 10 ml of hexol is added to the residue, the mixture is cooled, the crystals are filtered off. The output of 3.69 g (92%), so pl. 72-734, Ј -1 ppm ,

Found,%: C 38.61; H 4.54; R 7.72.

S26n38neVD; rg5gCalculated,%: C 38.95; H 4.72; R 7.74.

IR spectrum, V, cm: 980, 990 (DEW); 1175, 1200 (); 1570 ().

Thus, the proposed method allows to increase the yield of target products from 54 to 92-96%, carry out the process in one stage from the available starting materials and obtain a wide range of new compounds.

Claims (1)

Invention Formula The method of producing mercury complexes of N-phosphorylated thioamides of the general formula (0-SzN7 U30) 2 H / X "K X S II (from-с3н7-о) where R is CH3, C6Y5; X - O, S, by the interaction of a phosphoric derivative of a thioamide carboxylic acid with a mercury compound at boiling 5-15499556 g solvent, a different carboxylic acid thioamide, In order to simplify the process, and as a mercury compound - oxide increase in the yield of the target products, with their molar ratio and expanding their range, in ka-1: 0.75-3, and as a solvent Carbo-benzene or tetrachloride is used as a thioamide derivative. New acids use N-phosphoryl carbon.