N-(oxomethylidene)benzenesulfonamide

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 5-[4-[6-(8-aminonaphthalen-2-yloxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione (0.4 g) in anhydrous tetrahydrofuran (8 ml) was added benzenesulfonyl isocyanate (0.22 g) and the mixture was stirred at room temperature for 3 hours. The reaction mixture was concentrated. The residue was chromatographed on a silica gel column using ethyl acetate:n-hexane=3:1 as the eluant. The product was recrystallized from n-hexane to afford the title compound (55 mg, mp 199-205° C.). The reaction mixture was concentrated The residue was chromatographed on a silica gel column The product was recrystallized from n-hexane

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of the compound of Example 44 (0.511 g, 1.1 mmol) in dry THF (20 mL) was added sodium hydride (60% in mineral oil, 48 mg, 1.2 mmol), and the slurry heated at 40° C. under argon with stirring for 20 minutes. Phenylsulfonylisocyanate (160 μL, 1.2 mmol) was added and the mixture was stirred for 14 hours. The solvent was then removed by rotary evaporation to give the crude product. The solid material was washed twice with 20 mL CH2Cl2, and then twice with 20 mL MeoH: CH2Cl2 (1:1) to give the title compound (274 mg). the mixture was stirred for 14 hours The solvent was then removed by rotary evaporation to give the crude product The solid material was washed twice with 20 mL CH2Cl2

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of the compound of Example 44 (0.511 g, 1.1 mmol) in dry THF (20 mL) was added sodium hydride (60% in mineral oil, 48 mg, 1.2 mmol), and the slurry heated at 40° C. under argon with stirring for 20 minutes. Phenylsulfonylisocyanate (160 μL, 1.2 mmol) was added and the mixture was stirred for 14 hours. The solvent was then removed by rotary evaporation to give the crude product. The solid material was washed twice with 20 mL CH2Cl2, and then twice with 20 mL MeoH: CH2Cl2 (1:1) to give the title compound (274 mg). the mixture was stirred for 14 hours The solvent was then removed by rotary evaporation to give the crude product The solid material was washed twice with 20 mL CH2Cl2

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared in 83.5% yield from benzenesulfonyl isocyanate and 3,4-dichloroaniline following the procedure of Example 1, m.p. 194°-195° C.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4-(1,3-dioxobenzo[c]azolidin-2-yl)benzenesulfonamide in 660 uL of DMSO was added 60 mg (0.40 mmol) of DBU followed by 36 μl (0.33 mmol) of phenylsulfonylisocyanate. After stirring for 0.5 h, the mixture was poured into 1N HCl, cooled, and the precipitate was collected by filtration and dried under vacuum to give 137 mg (100%) of the titled compound. cooled the precipitate was collected by filtration dried under vacuum

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of the compound of Example 44 (0.511 g, 1.1 mmol) in dry THF (20 mL) was added sodium hydride (60% in mineral oil, 48 mg, 1.2 mmol), and the slurry heated at 40° C. under argon with stirring for 20 minutes. Phenylsulfonylisocyanate (160 μL, 1.2 mmol) was added and the mixture was stirred for 14 hours. The solvent was then removed by rotary evaporation to give the crude product. The solid material was washed twice with 20 mL CH2Cl2, and then twice with 20 mL MeoH: CH2Cl2 (1:1) to give the title compound (274 mg). MS m/z: 647 the mixture was stirred for 14 hours The solvent was then removed by rotary evaporation to give the crude product The solid material was washed twice with 20 mL CH2Cl2

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4-(1,3-dioxobenzo[c]azolidin-2-yl)benzenesulfonamide in 660 uL of DMSO was added 60 mg (0.40 mmol) of DBU followed by 36 μl (0.33 mmol) of phenylsulfonylisocyanate. After stirring for 0.5 h, the mixture was poured into 1N HCl, cooled, and the precipitate was collected by filtration and dried under vacuum to give 137 mg (100%) of the titled compound. cooled the precipitate was collected by filtration dried under vacuum

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 0.82 g. 2-Cyanoaziridine are dissolved in 8 ml. toluene and, while cooling with ice, 2 g. phenylsulphonyl isocyanate, dissolved in 10 ml. toluene, are added dropwise thereto. After further stirring the reaction mixture for 45 minutes at ambient temperature, the precipitated crystals are filtered off with suction, washed with diethyl ether and dried in a vacuum. There is thus obtained 1.45 g. (53% of theory) 1-(N-phenylsulphonyl-carbamoyl)2-cyanoaziridine in the form of white crystals; m.p. 103°-108° C. the precipitated crystals are filtered off with suction washed with diethyl ether dried in a vacuum

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Reaction of equimolar amounts of 5-isopropyl1,3-cyclohexanedione with benzenesulfonylisocyanate in benzene according to the procedure of Example 1 affords 5-ISOPROPYL-2-(N-BENZENESULFONYLCARBAMOYL)-1,3-CYCLOHEXANEDIONE, m.p. 112.5°-114° C. (corr.).