SU245120A1 - METHOD OF OBTAINING MERCAPTO ALKYLTRIAZOLE. TIONS OR MERCAPTOALKYLTRIAZOLONES - Google Patents

Description

This invention relates to the field of producing mercaptoalkyltriazolthions or mercaptoalkyltriazolones of the general formula I

n

C-C -N-RS

R / I II I

SH N WITH X

N /

I N

where X is O or S; R and R are hydrocarbon radicals. These compounds can be used in the pharmaceutical industry.

According to the proposed method, mercaptoalkyltriazolthions or mercaptoalkyltriazolones are obtained by recycling the thiazolidinediones or thiazolidonthionones of the general formula II

Y rC-N- R, N.

CX

R /

where X and Y-O or S; R and R are hydrocarbon radicals, hydrazine hydrate in water or aliphatic alcohol, for example, megyl alcohol. The final products are isolated and purified by conventional methods. Recycling is carried out at boiling.

Analytical data are consistent with the chemical structure of these compounds (by elemental and functional composition): they do not give positive reactions to the hydrazine group with Fehling and Tollens reagents (reduction of reagents with necessary nitrogen release), do not give derivatives with aldehydes under conditions of formation of hydrazones and azomethines , which indicates the absence of a primary amino group, and gives a positive reaction to the SH-group with sodium nitroprusside solution.

Example 1. Preparation of 5-mercaptomethyldihydro-1, 2,4-thiazol-3-one.

The thiazolidinedione is suspended in methanol and equimolecular amount of hydrazine hydrate is gradually added with vigorous stirring. Stirring is stopped

the mixture is kept for 2 hours at room temperature. Then, stirring rapidly, the reaction mass is acidified to pH 4 with 10% hydrochloric acid, brought to a boil and cooled. The precipitate is filtered and crystallized from water. Yield 60%. Colorless crystals with t. PL. 218 ° C (out of water).

Calculated,%: C 27.48; H 3.81; N 32.06; S 24.42.

Example 2. Preparation of 5-mercanthomethyl-dihydro-1, 2,4-triazole-3-one.

The isorovein is suspended at room temperature in methanol and an equimolecular amount of hydrazine hydrate is quickly added with stirring. The reaction mixture is heated to boiling and cooled. The precipitated crystalline product is filtered and recrystallized from water. Yield 85%. The product obtained by this method does not depress the melting point with the sample synthesized in Example 1.

Example 3. Obtaining mercaptoalkyltriazolthion by the reaction of cyclization of rhodanines.

The substituted rhodanine is suspended in water, brought to a boil, then, with vigorous stirring, hydrazine hydrate (in a 1: 1.5 molar ratio) is added quickly. The mixture is boiled for 15 minutes, cooled and a solution of 10% hydrochloric acid is quickly added until the acidic reaction to Congo. The precipitated colorless precipitate is filtered, crystallized from water. The output of 40-50%, depending on the nature of the substituents.

a) P {X S; Y 0; H), t. Pl. 220 ° C. Paideno,%: C, 24.75; H 3.61; N 28.65;

S 43.37.

CsHsNsSz.

%: C 24.49; P 3.40; N 28.57;

Calculated S 43,54. S; Y 0; R H, R C2H5), m. Pl.

b) II (X 128 ° C.%: C 34.38; P 5.48; N 24.10;

Found, S 36.57. CsHgNsSa.

Calculated,%: C 34.28; P 5.14; N 24.00; S 36.57.

c) II (X S; Y O; R CH3; R H), m. pl. 187 ° C.

Found,%: C 29.88; H 4.41; N 26.18; S 39,81.

C4H7N3S2.

Calculated,%: C 29.81; H 4.35; N 26.09; S 39.75.

d) II (X S; Y 0; R C2H3; R H), so pl. 16GS.

Found,%: C 34.57; H 5.39; N 24.16; S 36.35.

CsHgNsSz.

Calculated,%: C 34.28; H 5.14; N 24.00; S 36.57.

Subject invention

Claims (2)

1. Method of obtaining mercaptoalkyltriazolthions or mercaptoalkyltriazolones formulas H C - C - N - R R / I II I SH N C X N / where X is O or S; R and R are hydrocarbon radicals, characterized in that thiazolidinediones or triazolidonions are subjected to recycling by hydrazine hydrate in water or aliphatic alcohol, for example methyl, with the subsequent isolation and purification of the target products by conventional methods. 2. A method according to claim 1, characterized in that the cyclization is carried out at boiling.