(2-amino-2-sulfanylideneethyl) benzoate

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

Procedure: A mixture of 2-amino-2-thioxoethyl benzoate (7.6 g), 1,3-dichloro-2-propanone (7.6 g) and ethanol (100 mL) was heated under reflux for 4 hrs. The solvent was evaporated under reduced pressure, saturated aqueous sodium hydrogen carbonate was added to the residue and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate-hexane (1:5, v/v) to give (4-chloromethyl-1,3-thiazol-2-yl)methyl benzoate as a brown oil (7.3 g, yield 45%). was heated under reflux for 4 hrs The solvent was evaporated under reduced pressure, saturated aqueous sodium hydrogen carbonate was added to the residue the mixture was extracted with ethyl acetate The ethyl acetate layer was washed with saturated brine dried over anhydrous magnesium sulfate concentrated eluted with ethyl acetate-hexane (1:5

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

Procedure: A mixture of 2-amino-2-thioxoethyl benzoate (7.6 g), 1,3-dichloro-2-propanone (7.6 g) and ethanol (100 mL) was heated under reflux for 4 hrs. The solvent was evaporated under reduced pressure, saturated aqueous sodium hydrogen carbonate was added to the residue and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate-hexane (1:5, v/v) to give (4-chloromethyl-1,3-thiazol-2-yl)methyl benzoate as a brown oil (7.3 g, yield 45%). was heated under reflux for 4 hrs The solvent was evaporated under reduced pressure, saturated aqueous sodium hydrogen carbonate was added to the residue the mixture was extracted with ethyl acetate The ethyl acetate layer was washed with saturated brine dried over anhydrous magnesium sulfate concentrated eluted with ethyl acetate-hexane (1:5

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

Procedure: A mixture of 2-amino-2-thioxoethyl benzoate (7.6 g), 1,3-dichloro-2-propanone (7.6 g) and ethanol (100 mL) was heated under reflux for 4 hrs. The solvent was evaporated under reduced pressure, saturated aqueous sodium hydrogen carbonate was added to the residue and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate-hexane (1:5, v/v) to give (4-chloromethyl-1,3-thiazol-2-yl)methyl benzoate as a brown oil (7.3 g, yield 45%). was heated under reflux for 4 hrs The solvent was evaporated under reduced pressure, saturated aqueous sodium hydrogen carbonate was added to the residue the mixture was extracted with ethyl acetate The ethyl acetate layer was washed with saturated brine dried over anhydrous magnesium sulfate concentrated eluted with ethyl acetate-hexane (1:5

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

Procedure: A mixture of 9.14 g of 2-benzoyloxythioacetamide, 9 g of ethyl α-formyl-chloroacetate and 100 ml of dichloroethane was refluxed for 4 hours and after the addition of 4.5 g of ethyl β-formyl-chloroacetate, reflux was maintained for 2 hours. The mixture was cooled and was washed first with aqueous sodium carbonate and then water. The mixture was dried and the solvent was evaporated to obtain 14 g of raw product which was chromatographed over silica gel. Elution with a benzene-ethyl acetate mixture yielded 12.5 g of ethyl 2-benzoyloxymethyl-thiazole-5-carboxylate in the form of an oil. was refluxed for 4 hours reflux was maintained for 2 hours The mixture was cooled was washed first with aqueous sodium carbonate The mixture was dried the solvent was evaporated to obtain 14 g of raw product which was chromatographed over silica gel Elution with a benzene-ethyl acetate mixture