2-cyano-3-fluorobenzenesulfonyl chloride

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 110 mg of 2-cyano-3-fluoro-benzenesulfonyl chloride in 5 ml of tetrahydrofuran are treated with 61 mg of 3-oxo-pyrrolidine hydrochloride and with 0.14 ml of triethylamine, and the mixture is stirred for 16 hours at room temperature. The reaction mixture is concentrated in vacuo, the residue is solved in ethyl acetate and washed with a 1M HCl solution. Purification by Flash chromatography (eluent: cyclohexane/ethyl acetate 1:1) affords 21 mg of 2-fluoro-6-(3-oxo-pyrrolidine-1-sulfonyl)-benzonitrile. The reaction mixture is concentrated in vacuo washed with a 1M HCl solution Purification by Flash chromatography (eluent: cyclohexane/ethyl acetate 1:1)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 440 mg of 2-cyano-3-fluoro-benzenesulfonyl chloride in 10 ml of tetrahydrofuran are treated with 0.36 ml of thiazolidine and the mixture is stirred for 16 hours at room temperature. The reaction mixture is concentrated in vacuo. Purification by Flash chromatography (eluent: cyclohexane/ethyl acetate 1:1) followed by acidic washing with a 1M HCl solution affords 318 mg of 2-fluoro-6-(thiazolidine-3-sulfonyl)-benzonitrile. The reaction mixture is concentrated in vacuo Purification by Flash chromatography (eluent: cyclohexane/ethyl acetate 1:1) by acidic washing with a 1M HCl solution

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 100 mg of 2-cyano-3-fluoro-benzenesulfonyl chloride (EP33984 A1 19810819) is added to a solution of 0.85 ml of cyclopropylmethylamin in 3.5 ml of THF. After stirring for 3 hours at room temperature the reaction mixture is poured into water. The mixture is acidified with hydrochloric acid (˜pH3) and extracted three times with methylenchloride. The combined organic phases are dried (Na2SO4), filtered and concentrated. Preparative HPLC affords 16 mg of 4-fluoro-2-cyclopropylmethyl-1,2-benzisothiazol-3(2H)-imine 1,1-dioxide as an orange solid (m.p. 90-93° C.). extracted three times with methylenchloride The combined organic phases are dried (Na2SO4) filtered concentrated

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 110 mg of 2-cyano-3-fluoro-benzenesulfonyl chloride in 5 ml of tetrahydrofuran are treated with 61 mg of 3-oxo-pyrrolidine hydrochloride and with 0.14 ml of triethylamine, and the mixture is stirred for 16 hours at room temperature. The reaction mixture is concentrated in vacuo, the residue is solved in ethyl acetate and washed with a 1M HCl solution. Purification by Flash chromatography (eluent: cyclohexane/ethyl acetate 1:1) affords 21 mg of 2-fluoro-6-(3-oxo-pyrrolidine-1-sulfonyl)-benzonitrile. The reaction mixture is concentrated in vacuo washed with a 1M HCl solution Purification by Flash chromatography (eluent: cyclohexane/ethyl acetate 1:1)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 440 mg of 2-cyano-3-fluoro-benzenesulfonyl chloride in 10 ml of tetrahydrofuran are treated with 0.36 ml of thiazolidine and the mixture is stirred for 16 hours at room temperature. The reaction mixture is concentrated in vacuo. Purification by Flash chromatography (eluent: cyclohexane/ethyl acetate 1:1) followed by acidic washing with a 1M HCl solution affords 318 mg of 2-fluoro-6-(thiazolidine-3-sulfonyl)-benzonitrile. The reaction mixture is concentrated in vacuo Purification by Flash chromatography (eluent: cyclohexane/ethyl acetate 1:1) by acidic washing with a 1M HCl solution

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 110 mg of 2-cyano-3-fluoro-benzenesulfonyl chloride in 5 ml of tetrahydrofuran are treated with 61 mg of 3-oxo-pyrrolidine hydrochloride and with 0.14 ml of triethylamine, and the mixture is stirred for 16 hours at room temperature. The reaction mixture is concentrated in vacuo, the residue is solved in ethyl acetate and washed with a 1M HCl solution. Purification by Flash chromatography (eluent: cyclohexane/ethyl acetate 1:1) affords 21 mg of 2-fluoro-6-(3-oxo-pyrrolidine-1-sulfonyl)-benzonitrile. The reaction mixture is concentrated in vacuo washed with a 1M HCl solution Purification by Flash chromatography (eluent: cyclohexane/ethyl acetate 1:1)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 440 mg of 2-cyano-3-fluoro-benzenesulfonyl chloride in 10 ml of tetrahydrofuran are treated with 0.36 ml of thiazolidine and the mixture is stirred for 16 hours at room temperature. The reaction mixture is concentrated in vacuo. Purification by Flash chromatography (eluent: cyclohexane/ethyl acetate 1:1) followed by acidic washing with a 1M HCl solution affords 318 mg of 2-fluoro-6-(thiazolidine-3-sulfonyl)-benzonitrile. The reaction mixture is concentrated in vacuo Purification by Flash chromatography (eluent: cyclohexane/ethyl acetate 1:1) by acidic washing with a 1M HCl solution

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 5.2 ml of isopropylamine in 50 ml of diethyl ether cooled in an ice bath, a solution of 4.4 g of 2-cyano-3-fluorobenzenesulphonylchloride in 50 ml of diethylether was added dropwise while stirring; reaction temperature approx. 5° C. After leaving to stand at room temperature for one hour, the reaction mixture was washed twice with ice water, dried on anhydrous Na2SO4, filtered and evaporated to dryness. The desired product was obtained in a yield of 4.16 g; melting-point 97°-105° C. reaction temperature approx. 5° C After leaving the reaction mixture was washed twice with ice water dried on anhydrous Na2SO4 filtered evaporated to dryness

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 100 mg of 2-cyano-3-fluoro-benzenesulfonyl chloride (EP33984 A1 19810819) is added to a solution of 0.85 ml of cyclopropylmethylamin in 3.5 ml of THF. After stirring for 3 hours at room temperature the reaction mixture is poured into water. The mixture is acidified with hydrochloric acid (˜pH3) and extracted three times with methylenchloride. The combined organic phases are dried (Na2SO4), filtered and concentrated. Preparative HPLC affords 16 mg of 4-fluoro-2-cyclopropylmethyl-1,2-benzisothiazol-3(2H)-imine 1,1-dioxide as an orange solid (m.p. 90-93° C.). extracted three times with methylenchloride The combined organic phases are dried (Na2SO4) filtered concentrated