1,3-thiazolidin-2-one

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: Preparation took place in analogy to Example IV a from bromoacetonitrile and 2-thiazolidinone. The substance was employed as DMF-containing crude product in the next reaction. Preparation containing crude product in the next reaction

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-thiazolidinone (0.994 g, 9.64 mmol) in acetonitrile (10 ml) were added N-phthalimido-3-bromopropylamine (2.88 g, 10.7 mmol), potassium carbonate (1.64 g, 11.9 mmol), and 18-crown-6 (catalytic amount). The mixture was refluxed about 17 hours, solvent was removed in vacuo, and the resulting solid was redissolved in 1 M potassium chloride and dichloromethane (˜25 ml each). The aqueous phase was separated and extracted with 2×25 ml dichloromethane. The combined organic fraction was dried over sodium sulfate, filtered, and dried in vacuo. The crude product was recrystallized from acetone/methanol to give 1.54 g (55% yield). To a warmed solution of the phthalimido protected amine (1.53 g, 5.27 mmol) in 6:1 isopropanol:water was added sodium borohydride (1.01 g, 26.7 mmol), and the mixture was stirred at 60° C. for 22 hours. Glacial acetic acid (5.4 ml) was added, and the solution was stirred at 80° C. for 2 hours, then the solution was cooled and dried in vacuo. The product was redissolved in 6 N hydrochloric acid, washed with ether (2×30 ml), then dried in vacuo. The product was purified via recrystallization from hot water. The mixture was refluxed about 17 hours solvent was removed in vacuo the resulting solid was redissolved in 1 M potassium chloride The aqueous phase was separated extracted with 2×25 ml dichloromethane The combined organic fraction was dried over sodium sulfate filtered dried in vacuo The crude product was recrystallized from acetone/methanol to give 1.54 g (55% yield) the solution was stirred at 80° C. for 2 hours the solution was cooled dried in vacuo The product was redissolved in 6 N hydrochloric acid washed with ether (2×30 ml) dried in vacuo The product was purified via recrystallization from hot water

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

Procedure: To a solution of 2-thiazolidinone (4.15 g, 40.18 mmol) in acetonitrile (60 ml) were added potassium carbonate (13.3 g 96.2 mmol), N,N-dimethyl-3-aminopropyl chloride hydrochloride (7.63 g, 48.3 mmol), and 18-crown-6 (catalytic amount). The mixture was refluxed for 18 hours, solvent removed in vacuo, then redissolved in dichloromethane and 1 M potassium chloride (40 ml each). The aqueous phase was isolated and extracted twice with 30 ml portions of dichloromethane. The combined organic fraction was washed with saturated sodium chloride (˜50 ml), dried over sodium sulfate, filtered, and dried in vacuo. The crude product was purified via silica gel chromatography, using a 10:1 ratio of silica gel A, 200-425 mesh, and eluting with 5% methanol in chloroform, yielding 1.15 g (15%) pure product. The mixture was refluxed for 18 hours solvent removed in vacuo redissolved in dichloromethane The aqueous phase was isolated extracted twice with 30 ml portions of dichloromethane The combined organic fraction was washed with saturated sodium chloride (˜50 ml) dried over sodium sulfate filtered dried in vacuo The crude product was purified via silica gel chromatography eluting with 5% methanol in chloroform

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-thiazolidinone (0.994 g, 9.64 mmol) in acetonitrile (10 ml) were added N-phthalimido-3-bromopropylamine (2.88 g, 10.7 mmol), potassium carbonate (1.64 g, 11.9 mmol), and 18-crown-6 (catalytic amount). The mixture was refluxed about 17 hours, solvent was removed in vacuo, and the resulting solid was redissolved in 1 M potassium chloride and dichloromethane (˜25 ml each). The aqueous phase was separated and extracted with 2×25 ml dichloromethane. The combined organic fraction was dried over sodium sulfate, filtered, and dried in vacuo. The crude product was recrystallized from acetone/methanol to give 1.54 g (55% yield). To a warmed solution of the phthalimido protected amine (1.53 g, 5.27 mmol) in 6:1 isopropanol:water was added sodium borohydride (1.01 g, 26.7 mmol), and the mixture was stirred at 60° C. for 22 hours. Glacial acetic acid (5.4 ml) was added, and the solution was stirred at 80° C. for 2 hours, then the solution was cooled and dried in vacuo. The product was redissolved in 6 N hydrochloric acid, washed with ether (2×30 ml), then dried in vacuo. The product was purified via recrystallization from hot water. The mixture was refluxed about 17 hours solvent was removed in vacuo the resulting solid was redissolved in 1 M potassium chloride The aqueous phase was separated extracted with 2×25 ml dichloromethane The combined organic fraction was dried over sodium sulfate filtered dried in vacuo The crude product was recrystallized from acetone/methanol to give 1.54 g (55% yield) the solution was stirred at 80° C. for 2 hours the solution was cooled dried in vacuo The product was redissolved in 6 N hydrochloric acid washed with ether (2×30 ml) dried in vacuo The product was purified via recrystallization from hot water

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

Procedure: To a solution of 2-thiazolidinone (4.15 g, 40.18 mmol) in acetonitrile (60 ml) were added potassium carbonate (13.3 g 96.2 mmol), N,N-dimethyl-3-aminopropyl chloride hydrochloride (7.63 g, 48.3 mmol), and 18-crown-6 (catalytic amount). The mixture was refluxed for 18 hours, solvent removed in vacuo, then redissolved in dichloromethane and 1 M potassium chloride (40 ml each). The aqueous phase was isolated and extracted twice with 30 ml portions of dichloromethane. The combined organic fraction was washed with saturated sodium chloride (˜50 ml), dried over sodium sulfate, filtered, and dried in vacuo. The crude product was purified via silica gel chromatography, using a 10:1 ratio of silica gel A, 200-425 mesh, and eluting with 5% methanol in chloroform, yielding 1.15 g (15%) pure product. The mixture was refluxed for 18 hours solvent removed in vacuo redissolved in dichloromethane The aqueous phase was isolated extracted twice with 30 ml portions of dichloromethane The combined organic fraction was washed with saturated sodium chloride (˜50 ml) dried over sodium sulfate filtered dried in vacuo The crude product was purified via silica gel chromatography eluting with 5% methanol in chloroform

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

Procedure: A mixture containing 3.09 g (0.03 mol) of 2-thiazolidinone, 11.2 g of potassium carbonate, 1.8 g of potassium hydrogen carbonate, 0.5 ml of water, 30 ml of methyl isobutyl ketone and 6.5 g (0.03 mol) of nitrobenzyl bromide is refluxed for 6 hours, then cooled down and thoroughly mixed with 50 ml of water. The mixture is filtered and the clear filtrate is separated. The organic phase is washed with 10 ml of water, dried and evaporated. The oily residue is recrystallized from ethanol to give 2.65 g (37.0%) of the title compound, m.p.: 92°-93° C. is refluxed for 6 hours cooled down The mixture is filtered the clear filtrate is separated The organic phase is washed with 10 ml of water dried evaporated The oily residue is recrystallized from ethanol

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

Procedure: A mixture containing 3.09 g (0.03 mol) of 2-thiazolidinone, 11.2 g of potassium carbonate, 1.8 g of potassium hydrogen carbonate, 0.5 ml of water, 30 ml of methyl isobutyl ketone and 3.0 ml (0.033 mol) of benzyl bromide is refluxed for 7 hours. After cooling down, the reaction mixture is washed twice with 30 ml of water each, the organic phase is dried and evaporated. The yellow oily product (which solidifies on standing) may be purified by column chromatography (by using Kieselgel 60 of 230-400 mesh as sorbent and chloroform as eluent) to give 3.2 g (55.2%) of the title compound, m.p.: 50°-51° C. is refluxed for 7 hours After cooling down the reaction mixture is washed twice with 30 ml of water each, the organic phase is dried evaporated The yellow oily product (which solidifies on standing) may be purified by column chromatography (by using Kieselgel 60 of 230-400 mesh as sorbent and chloroform as eluent)

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-thiazolidinone (0.994 g, 9.64 mmol) in acetonitrile (10 ml) were added N-phthalimido-3-bromopropylamine (2.88 g, 10.7 mmol), potassium carbonate (1.64 g, 11.9 mmol), and 18-crown-6 (catalytic amount). The mixture was refluxed about 17 hours, solvent was removed in vacuo, and the resulting solid was redissolved in 1 M potassium chloride and dichloromethane (˜25 ml each). The aqueous phase was separated and extracted with 2×25 ml dichloromethane. The combined organic fraction was dried over sodium sulfate, filtered, and dried in vacuo. The crude product was recrystallized from acetone/methanol to give 1.54 g (55% yield). To a warmed solution of the phthalimido protected amine (1.53 g, 5.27 mmol) in 6:1 isopropanol:water was added sodium borohydride (1.01 g, 26.7 mmol), and the mixture was stirred at 60° C. for 22 hours. Glacial acetic acid (5.4 ml) was added, and the solution was stirred at 80° C. for 2 hours, then the solution was cooled and dried in vacuo. The product was redissolved in 6 N hydrochloric acid, washed with ether (2×30 ml), then dried in vacuo. The product was purified via recrystallization from hot water. The mixture was refluxed about 17 hours solvent was removed in vacuo the resulting solid was redissolved in 1 M potassium chloride The aqueous phase was separated extracted with 2×25 ml dichloromethane The combined organic fraction was dried over sodium sulfate filtered dried in vacuo The crude product was recrystallized from acetone/methanol to give 1.54 g (55% yield) the solution was stirred at 80° C. for 2 hours the solution was cooled dried in vacuo The product was redissolved in 6 N hydrochloric acid washed with ether (2×30 ml) dried in vacuo The product was purified via recrystallization from hot water

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

Procedure: To a solution of 2-thiazolidinone (4.15 g, 40.18 mmol) in acetonitrile (60 ml) were added potassium carbonate (13.3 g 96.2 mmol), N,N-dimethyl-3-aminopropyl chloride hydrochloride (7.63 g, 48.3 mmol), and 18-crown-6 (catalytic amount). The mixture was refluxed for 18 hours, solvent removed in vacuo, then redissolved in dichloromethane and 1 M potassium chloride (40 ml each). The aqueous phase was isolated and extracted twice with 30 ml portions of dichloromethane. The combined organic fraction was washed with saturated sodium chloride (˜50 ml), dried over sodium sulfate, filtered, and dried in vacuo. The crude product was purified via silica gel chromatography, using a 10:1 ratio of silica gel A, 200˜425 mesh, and eluting with 5% methanol in chloroform, yielding 1.15 g (15%) pure product. The mixture was refluxed for 18 hours solvent removed in vacuo redissolved in dichloromethane The aqueous phase was isolated extracted twice with 30 ml portions of dichloromethane The combined organic fraction was washed with saturated sodium chloride (˜50 ml) dried over sodium sulfate filtered dried in vacuo The crude product was purified via silica gel chromatography eluting with 5% methanol in chloroform

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

Procedure: A mixture containing 3.09 g (0.03 mol) of 2-thiazolidinone, 11.2 g (0.081 mol) of potassium carbonate, 1.8 g (0.018 mol) of potassium hydrogen carbonate, 0.5 ml (0.027 mol) of water and 6.47 g (0.033 mol) of 2-bromomethylbenzonitrile in 30 ml of methyl isobutyl ketone is refluxed for 5 hours, then cooled down. After adding 30 ml of water the mixture is stirred for 30 minutes, the insoluble precipitate is filtered off, washed twice with 10 ml of water each and dried. After recrystallizing 4.71 g of crude product from 20 ml of ethanol under simultaneous clarification with activated carbon 3.39 g (51.8%) of white, crystalline title compound are obtained, m.p.: 116°-117° C. is refluxed for 5 hours cooled down the insoluble precipitate is filtered off washed twice with 10 ml of water each and dried After recrystallizing 4.71 g of crude product from 20 ml of ethanol under simultaneous clarification with activated carbon 3.39 g (51.8%) of white, crystalline title compound are obtained