1,3-thiazolidine-2-thione

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

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

Procedure: A mixture of 12 g. of thiazolidine-2-thione, and 16 g. of 1-bromo-3-chloro propane in 100 ml. of acetonitrile is refluxed for 12 hours, cooled and the product removed by filtration. Recrystallization from ethanol gives 2,3,5,6-tetrahydrothiazolo[2,3-b]-(1,3)-thiazinium bromide. A mixture of 12 g cooled the product removed by filtration Recrystallization from ethanol

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

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of elaidic acid (2.0 g, 7.1 mmol), DMAP (86 mg, 0.7 mmol), 1,3-thiazolidine-2-thione (1.0 g, 8.4 mmol) and DCC (1.7 g, 8.2 mmol) in dichloromnethane (20 ml) was stirred under N2 at 0° C. for 1 hour and then at ambient temperature for another 5 hours. Additional DCC (41 mg, 0.2 mmol) was added, andthe reaction was stirred at the same temperature for 2 hours. Work up followed by flash chromatography (SiO2; carbon tetrachloride-chloroform 1:0, 1:1, 0:1) gave 2.56 g (94%) of the title compound as a yellow waxy solid. at ambient temperature for another 5 hours andthe reaction was stirred at the same temperature for 2 hours

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

Procedure: A mixture of 12 g. of thiazolidine-2-thione, and 16 g. of 1-bromo-3-chloro propane in 100 ml. of acetonitrile is refluxed for 12 hours, cooled and the product removed by filtration. Recrystallization from ethanol gives 2,3,5,6-tetrahydrothiazolo[2,3-b]-(1,3)-thiazinium bromide. A mixture of 12 g cooled the product removed by filtration Recrystallization from ethanol

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

Procedure: To 15 ml of dimethylformamide were dissolved 3,5-dinitrobenzoyl chloride (2.5 g) and 1,3-thiazolidine-2-thione (1.3 g). To the solution was added dropwise a solution of triethyl amine (1.2 g) and dimethylformamide (2 ml) under ice-cooling. The mixture was stirred under ice-cooling for 1 hour and at room temperature for 5 hours. The reaction mixture was filtered and the solvent was removed at a reduced pressure. To the residue was added water and the insolubles were filtered off. The filtrate was washed with cold methanol and then with ether to obtain crude crystals. Recrystallization from toluene gives 2.4 g of the desired compound as yellow needle crystals (yield 76.7%). cooling The reaction mixture was filtered the solvent was removed at a reduced pressure To the residue was added water the insolubles were filtered off The filtrate was washed with cold methanol with ether to obtain crude crystals Recrystallization from toluene

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

Procedure: To a solution of 4-nitrobenzoyl chloride (3.1 g) and tetrahydrofuran (50 ml) were added 1,3-thiazolidine-2-thione (2.0 g) and triethyl amine (2.5 g). The mixture was stirred at 50° C. for 30 minutes under nitrogen atmosphere. The reaction mixture was filtered and the solvent was removed at a reduced pressure. To the residue was added water, and the solution is extracted with dichloromethane. The extract was washed with a saturated aqueous solution of sodium chloride and dried with use of Glauber's salt. The solvent was distilled off and the resulting crystals were purified by silica gel column chromatography (developer: dichloromethane) and recrystallized from dichloromethane to obtain 3.3 g of the desired compound as yellow needle crystals (yield 82.5%). The reaction mixture was filtered the solvent was removed at a reduced pressure To the residue was added water the solution is extracted with dichloromethane The extract was washed with a saturated aqueous solution of sodium chloride dried with use of Glauber's salt The solvent was distilled off the resulting crystals were purified by silica gel column chromatography (developer: dichloromethane) recrystallized from dichloromethane

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

Procedure: A mixture of 12 g. of thiazolidine-2-thione, and 16 g. of 1-bromo-3-chloro propane in 100 ml. of acetonitrile is refluxed for 12 hours, cooled and the product removed by filtration. Recrystallization from ethanol gives 2,3,5,6-tetrahydrothiazolo[2,3-b]-(1,3)-thiazinium bromide. A mixture of 12 g cooled the product removed by filtration Recrystallization from ethanol