SU1587050A1 - Derivatives of (7-bromobenzo-2,1,3-thiadiazol-4-sulfonyl)-amine as intermediate products in synthesis of benzamide displaying antihelmint activity - Google Patents

Abstract

The invention relates to heterocyclic compounds, in particular to 2 - [(7-bromobenzo-2,1,3-thiadiazole-4-sulfonyl) amino benzoic acid (Ia) or 5-bromobenzoic acid (Ib), which can be used in as intermediate products in the synthesis of 2 - [(7-bromobenzo-2,1,3-thiadiazole-4-sulfonyl) amino] -5-bromo-N- (4-chlorophenyl) benzamide, which has anthelmintic activity. The goal is the discovery of new intermediates. The preparation is carried out by the reaction of 7-bromo-4-chlorosulfonylbenzo-2,1,3-thiadiazole with anthranilic acid in an aqueous solution of sodium carbonate. Yield,%, So., ° C, Gross-f-la. For Compound Ia-80, 224-225, C 13H 8BRN 3O 4S 2

For Compound Ib-86, 193-195, C 13H 7BR 2N 3O 4S 2.

Description

Gris is heated before stirring jj for 12 hours. The precipitate is filtered off, washed thoroughly with water. Yield 7.8 g (65%), T.Sh1, 254-255 0 (from acetic acid).

The obtained 7.8 tons of the target substance is dissolved in 13 ml of dimethylformamide (DMF) with heating, cooled and the solution is poured into 25 ml of isopropanol, then 100 ml of water are added with over 20

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1) The solution is dissolved in a mixture of 30 ml of dimethylformamide and 10 ml of ice-cold acetic acid. The resulting solution is cooled to 40 ° C and a solution of 1.2 ml of 3.75 g, 0.0234 mol) of bromine in 5 mp of acetic acid is added dropwise with stirring. The mixture is stirred for 30 minutes. The mixture is poured into 250 ml of cold water; the precipitate is initially oily and becomes crystalline on standing. Its 25 s |) is filtered off, washed with water and 1 is recrystallized from 25 ml of isopropanol. Yield 8.5 g (86%), m.p. | 93-195 p.

: Found,%: C 31.23; H 1.72; $ g 32.49; N 8.36; S 13.03.

; 2: Calculated,%: C 31.66; H 1.43;

fer 32.41; N 8.52; S 13.00.

PRI me R 3. Getting the drug g1460 - 2 (7-bromobenzo-2,1, 3-thiadia-5ol-4-sulfonyl) amino} -5-6poM-N- (4-. I-chlorophenyl) benzamide .

Stage I. Preparation of 2-C (7-bromobenzo-2,1,3-thiadiazole-4-sulfonyl) amino 5-bromobenzoic acid acid chloride.

A mixture of 9.86 g (0.02 mol) of 2- (7- -bromobenzo-2,1,3-thiadiazole-4-sulfonyl) amino 5-bromobenzoic acid and 15 ml of thionyl chloride is boiled for 1 hour. Excess thionichloride is removed in vacuo, 15 ml of benzene are added twice and removed in vacuo to dryness. The acid chloride remaining in the flask is used in the next step without further purification.

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Editor N. Rogulich

Compiled by T. Raevska Tehred L. Oliynyk

stirring, fine crystalline precipitate, filtered, washed with water. The dispersion of powder 4-6 m, so pl. 255-256 С „

Found,%: C 38.36; H 2.12; Br 26.18; C1 5.81; N 8.65; S 10.50.

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Calculated,%: C 37.86; H 1.84; Br 26.52; C1 5.88; N 9.29; S 10.64.

This product has high anti-helminth activity.

Claims (1)

Invention Formula Derivatives of (7-bromobenzo-2,1,3-thiadiazole-4-sulfonyl) amine of the general formula soon where R is hydrogen or bromine, as intermediates, in the synthesis of 2- (7-bromobenzo-2,1,3-thiazazol-4-sulfonyl) amino -5-6pOM-N- (4- chlorophenyl) benzamide with anti-helminth activity. Proofreader A. Osaulenko 0 five 0 stirring, fine crystalline precipitate, filtered, washed with water. The dispersion of powder 4-6 m, so pl. 255-256 С „ Found,%: C 38.36; H 2.12; Br 26.18; C1 5.81; N 8.65; S 10.50. . Calculated,%: C 37.86; H 1.84; Br 26.52; C1 5.88; N 9.29; S 10.64. This product has high anti-helminth activity. Invention Formula Derivatives of (7-bromobenzo-2,1,3-thiadiazole-4-sulfonyl) amine of the general formula soon where R is hydrogen or bromine, as intermediates, in the synthesis of 2- (7-bromobenzo-2,1,3-thiazazol-4-sulfonyl) amino -5-6pOM-N- (4- chlorophenyl) benzamide with anti-helminth activity. Proofreader A. Osaulenko