N-Aminorhodanine

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

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

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of the methiodide of 5-chloro-N-methyl-N-phenyl-1,3-benzodithiol-2-iminium iodide (1.9 g), sodium carbonate (121 mg), N-aminorhodanine (338 mg) and dimethylformamide (20 ml) is heated at 50° C for 3 hours. The mixture is poured into water and the precipitate which forms is filtered and washed with water. The product is recrystallized from dimethylformamide to yield 600 mg of the title compound, melting point 312°-314° C. the precipitate which forms is filtered washed with water The product is recrystallized from dimethylformamide

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of the methiodide of 5-chloro-N-methyl-N-phenyl-1,3-benzodithiol-2-iminium iodide (1.9 g), sodium carbonate (121 mg), N-aminorhodanine (338 mg) and dimethylformamide (20 ml) is heated at 50° C for 3 hours. The mixture is poured into water and the precipitate which forms is filtered and washed with water. The product is recrystallized from dimethylformamide to yield 600 mg of the title compound, melting point 312°-314° C. the precipitate which forms is filtered washed with water The product is recrystallized from dimethylformamide

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

Procedure: A mixture of 4,6-bis(1,1-dimethylethyl)-5-hydroxy-2-pyrimidine carboxaldehyde (1.00 g, 4.23 mmol), sodium acetate (1.36 g, 16.6 mmol), and 3-aminorhodanine (0.63 g, 4.3 mmol) in glacial acetic acid (15 mL), under nitrogen atmosphere, is warmed to reflux and refluxed 7 hours. This mixture is then cooled to room temperature and stirred 16 hours. After stirring, the reaction mixture is diluted with a 1:2 mixture of ethanol and water and extracted with ethyl acetate. The combined organic extracts are washed with water, aqueous 0.2N hydrochloric acid solution, and brine. The organic phase is dried over magnesium sulfate, concentrated, and purified by flash chromatography (SiO2, 20% ethyl acetate/hexane) followed by recrystallization from methanol and water to give 0.42 g (27%) of the title compound, mp 194°-196° C. under nitrogen atmosphere, is warmed to reflux refluxed 7 hours After stirring extracted with ethyl acetate The combined organic extracts are washed with water, aqueous 0.2N hydrochloric acid solution, and brine The organic phase is dried over magnesium sulfate concentrated purified by flash chromatography (SiO2, 20% ethyl acetate/hexane) followed by recrystallization from methanol and water

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

Procedure: A mixture of 4,6-bis(1,1-dimethylethyl)-5-hydroxy-2-pyrimidine carboxaldehyde (1.00 g, 4.23 mmol), sodium acetate (1.36 g, 16.6 mmol), and 3-aminorhodanine (0.63 g, 4.3 mmol) in glacial acetic acid (15 mL), under nitrogen atmosphere, is warmed to reflux and refluxed 7 hours. This mixture is then cooled to room temperature and stirred 16 hours. After stirring, the reaction mixture is diluted with a 1:2 mixture of ethanol and water and extracted with ethyl acetate. The combined organic extracts are washed with water, aqueous 0.2N hydrochloric acid solution, and brine. The organic phase is dried over magnesium sulfate, concentrated, and purified by flash chromatography (SiO2, 20% ethyl acetate/hexane) followed by recrystallization from methanol and water to give 0.42 g (27%) of the title compound, mp 194°-196° C. under nitrogen atmosphere, is warmed to reflux refluxed 7 hours After stirring extracted with ethyl acetate The combined organic extracts are washed with water, aqueous 0.2N hydrochloric acid solution, and brine The organic phase is dried over magnesium sulfate concentrated purified by flash chromatography (SiO2, 20% ethyl acetate/hexane) followed by recrystallization from methanol and water

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

Procedure: A mixture of 4,6-bis(1,1-dimethylethyl)-5-hydroxy-2-pyrimidine carboxaldehyde (1.00 g, 4.23 mmol), sodium acetate (1.36 g, 16.6 mmol), and 3-aminorhodanine (0.63 g, 4.3 mmol) in glacial acetic acid (15 mL), under nitrogen atmosphere, is warmed to reflux and refluxed 7 hours. This mixture is then cooled to room temperature and stirred 16 hours. After stirring, the reaction mixture is diluted with a 1:2 mixture of ethanol and water and extracted with ethyl acetate. The combined organic extracts are washed with water, aqueous 0.2N hydrochloric acid solution, and brine. The organic phase is dried over magnesium sulfate, concentrated, and purified by flash chromatography (SiO2, 20% ethyl acetate/hexane) followed by recrystallization from methanol and water to give 0.42 g (27%) of the title compound, mp 194°-196° C. under nitrogen atmosphere, is warmed to reflux refluxed 7 hours After stirring extracted with ethyl acetate The combined organic extracts are washed with water, aqueous 0.2N hydrochloric acid solution, and brine The organic phase is dried over magnesium sulfate concentrated purified by flash chromatography (SiO2, 20% ethyl acetate/hexane) followed by recrystallization from methanol and water

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

Procedure: To a solution of 3-aminorhodanine (1.00 g) in ethanol (20 ml) were added 4-phenoxybenzaldehyde (1.47 g) and piperidine (57 mg), and the mixture was heated with reflux for 2 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: chloroform) to give 3-amino-5-(4-phenoxybenzylidene)-2-thioxothiazolidin-4-one (1.52 g). the mixture was heated with reflux for 2 hr The reaction mixture was concentrated under reduced pressure the residue was purified by silica gel column chromatography (eluent: chloroform)

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of o-sulfobenzimide (5.00 g) in dioxane (20 ml) were added thionyl chloride (7.5 ml) and dimethylformamide (0.25 ml), and the mixture was stirred overnight at 110° C. The reaction mixture was concentrated under reduced pressure, and to the residue was added toluene (20 ml) to give 3-chloro-1,2-benzisothiazole 1,1-dioxide (3.77 g) as crystals. The obtained 3-chloro-1,2-benzisothiazole 1,1-dioxide (3.77 g) was dissolved in dioxane (20 ml), 3-aminorhodanine (2.77 g) was added thereto, and the mixture was stirred at 110° C. for 1 hr. The reaction mixture was concentrated under reduced pressure, and to the residue was added chloroform (20 ml) to give 3-[(4-oxo-2-thioxothiazolidin-3-yl)amino]-1,2-benzisothiazole 1,1-dioxide (3.56 g). The reaction mixture was concentrated under reduced pressure to the residue was added chloroform (20 ml)

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

Procedure: A mixture of 3-aminorhodanine (148 mg, 1.00 mmol), 1-(3,4-dimethylphenyl)-5-hydroxy-3-methyl-1H-pyrazole-4-carbaldehyde (230 mg, 1.00 mmol) and ethanol (10 mL) was stirred 96 h. The solid was filtered, washed with ethanol and ether and dried. A mixture of the resulting crude imine (80 mg, 0.222 mmol), piperidine (2 mg, 0.022 mmol), 4-formylbenzoic acid (33 mg, 0.222 mmol), benzoic acid (3 mg, 0.022 mmol) and toluene (10 mL) was heated under reflux for 6 h in an apparatus fitted with a Dean and Stark separator to remove water. After cooling, the solid was filtered off, washed with toluene and ether, and purified by reverse phase HPLC (CombiPrep ODS-A, 10-90% acetonitrile/water+0.1% trifluoroacetic acid) to give the title compound (18 mg, 16%) as a solid. LCMS, m/e 493 [M+H]+. The solid was filtered washed with ethanol and ether dried was heated under reflux for 6 h in an apparatus fitted with a Dean and Stark separator to remove water After cooling the solid was filtered off washed with toluene and ether purified by reverse phase HPLC (CombiPrep ODS-A, 10-90% acetonitrile/water+0.1% trifluoroacetic acid)

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

Procedure: An admixture of 4.7 grams of 4-[4'-(2"-hydroxyethyl)piperazino]benzaldehyde (0.02 mol), 3.0 grams of 3-aminorhodanine (0.02 mol), toluene (30 mL), and glacial acetic acid (5 mL) was refluxed for 4 hours. The admixture was then cooled to room temperature and the solvent was decanted. The remaining paste was triturated with ethanol and then filtered off and dried. the solvent was decanted The remaining paste was triturated with ethanol filtered off dried