2-(dimethylamino)ethanethioamide

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

Procedure: A mixture of 118 g. of dimethylaminothioacetamide, 92.4 g. of sodium bicarbonate, 140 g. of 1,3-dichloropropanone and 600 ml. of 1,2-dichloroethane was stirred at ambient temperature for 24 hours, and was then filtered. To the filtrate, at ice-bath temperature, was added 131 g. of thionyl chloride, dropwise. One hundred ml. of additional 1,2-dichloroethane was added, and the mixture was stirred for 2 hours at ambient temperature and then for 1 hour under reflux. The mixture was then chilled overnight, warmed to ambient temperature and filtered. The filter cake was washed with 200 ml. of 1,2-dichloroethane and blown dry, and the solids were dried overnight under vacuum to obtain 202.5 g. of the desired product, substantially identical to the product of Example 5. A mixture of 118 g was then filtered To the filtrate, at ice-bath temperature, was added 131 g of additional 1,2-dichloroethane was added for 1 hour under reflux The mixture was then chilled overnight warmed to ambient temperature filtered The filter cake was washed with 200 ml of 1,2-dichloroethane and blown dry, and the solids were dried overnight under vacuum to obtain 202.5 g

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-(Dimethylamino)ethanethioamide (0.382 g, 3.24 mmol), 1,3-dichloroacetone (0.453 g, 3.56 mmol) and sodium bicarbonate (0.301 g, 3.56 mmol) was stirred in 1,2-dichloroethane (4 mL) at room temperature for 24 h. The reaction mixture was filtered and the filter cake was washed with 1,2-dichloroethane. The filtrate was added dropwise to a cooled (ice bath) solution of thionyl chloride (0.260 mL, 3.56 mmol) in 1,2-dichloroethane (2 mL). The solution was stirred at 70° C. for 0.5 h and then cooled to room temperature. The brown mixture was filtered and washed with 1,2-dichloroethane to afford N-{[4-(chloromethyl)-1,3-thiazol-2-yl]methyl}-N,N-dimethylamine hydrochloride as a brown solid (0.550 g, 2.42 mmol, 75% yield). 1H NMR (400 MHz; D2O): 2.79 (s, 6H); 4.52 (s, 2H); 4.61 (s, 2H); 7.60 (s, 1H). The reaction mixture was filtered the filter cake was washed with 1,2-dichloroethane The filtrate was added dropwise to cooled to room temperature The brown mixture was filtered washed with 1,2-dichloroethane

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-(Dimethylamino)ethanethioamide (0.382 g, 3.24 mmol), 1,3-dichloroacetone (0.453 g, 3.56 mmol) and sodium bicarbonate (0.301 g, 3.56 mmol) was stirred in 1,2-dichloroethane (4 mL) at room temperature for 24 h. The reaction mixture was filtered and the filter cake was washed with 1,2-dichloroethane. The filtrate was added dropwise to a cooled (ice bath) solution of thionyl chloride (0.260 mL, 3.56 mmol) in 1,2-dichloroethane (2 mL). The solution was stirred at 70° C. for 0.5 h and then cooled to room temperature. The brown mixture was filtered and washed with 1,2-dichloroethane to afford N-{[4-(chloromethyl)-1,3-thiazol-2-yl]methyl}-N,N-dimethylamine hydrochloride as a brown solid (0.550 g, 2.42 mmol, 75% yield). 1H NMR (400 MHz; D2O): 2.79 (s, 6H); 4.52 (s, 2H); 4.61 (s, 2H); 7.60 (s, 1H). The reaction mixture was filtered the filter cake was washed with 1,2-dichloroethane The filtrate was added dropwise to cooled to room temperature The brown mixture was filtered washed with 1,2-dichloroethane

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

Procedure: A mixture of 118 g. of dimethylaminothioacetamide, 92.4 g. of sodium bicarbonate, 140 g. of 1,3-dichloropropanone and 600 ml. of 1,2-dichloroethane was stirred at ambient temperature for 24 hours, and was then filtered. To the filtrate, at ice-bath temperature, was added 131 g. of thionyl chloride, dropwise. One hundred ml. of additional 1,2-dichloroethane was added, and the mixture was stirred for 2 hours at ambient temperature and then for 1 hour under reflux. The mixture was then chilled overnight, warmed to ambient temperature and filtered. The filter cake was washed with 200 ml. of 1,2-dichloroethane and blown dry, and the solids were dried overnight under vacuum to obtain 202.5 g. of the desired product, substantially identical to the product of Example 5. A mixture of 118 g was then filtered To the filtrate, at ice-bath temperature, was added 131 g of additional 1,2-dichloroethane was added for 1 hour under reflux The mixture was then chilled overnight warmed to ambient temperature filtered The filter cake was washed with 200 ml of 1,2-dichloroethane and blown dry, and the solids were dried overnight under vacuum to obtain 202.5 g

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

Procedure: A mixture of 118 g. of dimethylaminothioacetamide, 92.4 g. of sodium bicarbonate, 140 g. of 1,3-dichloropropanone and 600 ml. of 1,2-dichloroethane was stirred at ambient temperature for 24 hours, and was then filtered. To the filtrate, at ice-bath temperature, was added 131 g. of thionyl chloride, dropwise. One hundred ml. of additional 1,2-dichloroethane was added, and the mixture was stirred for 2 hours at ambient temperature and then for 1 hour under reflux. The mixture was then chilled overnight, warmed to ambient temperature and filtered. The filter cake was washed with 200 ml. of 1,2-dichloroethane and blown dry, and the solids were dried overnight under vacuum to obtain 202.5 g. of the desired product, substantially identical to the product of Example 5. A mixture of 118 g was then filtered To the filtrate, at ice-bath temperature, was added 131 g of additional 1,2-dichloroethane was added for 1 hour under reflux The mixture was then chilled overnight warmed to ambient temperature filtered The filter cake was washed with 200 ml of 1,2-dichloroethane and blown dry, and the solids were dried overnight under vacuum to obtain 202.5 g

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-(Dimethylamino)ethanethioamide (0.382 g, 3.24 mmol), 1,3-dichloroacetone (0.453 g, 3.56 mmol) and sodium bicarbonate (0.301 g, 3.56 mmol) was stirred in 1,2-dichloroethane (4 mL) at room temperature for 24 h. The reaction mixture was filtered and the filter cake was washed with 1,2-dichloroethane. The filtrate was added dropwise to a cooled (ice bath) solution of thionyl chloride (0.260 mL, 3.56 mmol) in 1,2-dichloroethane (2 mL). The solution was stirred at 70° C. for 0.5 h and then cooled to room temperature. The brown mixture was filtered and washed with 1,2-dichloroethane to afford N-{[4-(chloromethyl)-1,3-thiazol-2-yl]methyl}-N,N-dimethylamine hydrochloride as a brown solid (0.550 g, 2.42 mmol, 75% yield). 1H NMR (400 MHz; D2O): 2.79 (s, 6H); 4.52 (s, 2H); 4.61 (s, 2H); 7.60 (s, 1H). The reaction mixture was filtered the filter cake was washed with 1,2-dichloroethane The filtrate was added dropwise to cooled to room temperature The brown mixture was filtered washed with 1,2-dichloroethane

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-(Dimethylamino)ethanethioamide (0.382 g, 3.24 mmol), 1,3-dichloroacetone (0.453 g, 3.56 mmol) and sodium bicarbonate (0.301 g, 3.56 mmol) was stirred in 1,2-dichloroethane (4 mL) at room temperature for 24 h. The reaction mixture was filtered and the filter cake was washed with 1,2-dichloroethane. The filtrate was added dropwise to a cooled (ice bath) solution of thionyl chloride (0.260 mL, 3.56 mmol) in 1,2-dichloroethane (2 mL). The solution was stirred at 70° C. for 0.5 h and then cooled to room temperature. The brown mixture was filtered and washed with 1,2-dichloroethane to afford N-{[4-(chloromethyl)-1,3-thiazol-2-yl]methyl}-N,N-dimethylamine hydrochloride as a brown solid (0.550 g, 2.42 mmol, 75% yield). 1H NMR (400 MHz; D2O): 2.79 (s, 6H); 4.52 (s, 2H); 4.61 (s, 2H); 7.60 (s, 1H). The reaction mixture was filtered the filter cake was washed with 1,2-dichloroethane The filtrate was added dropwise to cooled to room temperature The brown mixture was filtered washed with 1,2-dichloroethane

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-(Dimethylamino)ethanethioamide (0.382 g, 3.24 mmol), 1,3-dichloroacetone (0.453 g, 3.56 mmol) and sodium bicarbonate (0.301 g, 3.56 mmol) was stirred in 1,2-dichloroethane (4 mL) at room temperature for 24 h. The reaction mixture was filtered and the filter cake was washed with 1,2-dichloroethane. The filtrate was added dropwise to a cooled (ice bath) solution of thionyl chloride (0.260 mL, 3.56 mmol) in 1,2-dichloroethane (2 mL). The solution was stirred at 70° C. for 0.5 h and then cooled to room temperature. The brown mixture was filtered and washed with 1,2-dichloroethane to afford N-{[4-(chloromethyl)-1,3-thiazol-2-yl)methyl}-N,N-dimethylamine hydrochloride as a brown solid (0.550 g, 2.42 mmol, 75% yield). 1H NMR (400 MHz; D2O): 2.79 (s, 6H); 4.52 (s, 2H); 4.61 (s, 2H); 7.60 (s, 1H). The reaction mixture was filtered the filter cake was washed with 1,2-dichloroethane The filtrate was added dropwise to cooled to room temperature The brown mixture was filtered washed with 1,2-dichloroethane

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-(Dimethylamino)ethanethioamide (0.382 g, 3.24 mmol), 1,3-dichloroacetone (0.453 g, 3.56 mmol) and sodium bicarbonate (0.301 g, 3.56 mmol) was stirred in 1,2-dichloroethane (4 mL) at room temperature for 24 h. The reaction mixture was filtered and the filter cake was washed with 1,2-dichloroethane. The filtrate was added dropwise to a cooled (ice bath) solution of thionyl chloride (0.260 mL, 3.56 mmol) in 1,2-dichloroethane (2 mL). The solution was stirred at 70° C. for 0.5 h and then cooled to room temperature. The brown mixture was filtered and washed with 1,2-dichloroethane to afford N-{[4-(chloromethyl)-1,3-thiazol-2-yl]methyl}-N,N-dimethylamine hydrochloride as a brown solid (0.550 g, 2.42 mmol, 75% yield). 1H NMR (400 MHz; D2O): 2.79 (s, 6H); 4.52 (s, 2H); 4.61 (s, 2H); 7.60 (s, 1H). The reaction mixture was filtered the filter cake was washed with 1,2-dichloroethane The filtrate was added dropwise to cooled to room temperature The brown mixture was filtered washed with 1,2-dichloroethane

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

Procedure: A mixture of 1,2-bis(4-methoxyphenyl)-2-chloroethanone (11.05 g) and 2-(N,N-dimethylamino)ethanethioamide 5.39 g) in ethanol (100 ml) was refluxed for 2 hours. After allowing to cool to room temperature, the solvent was evaporated in vacuo, and the residue was dissolved in chloroform (500 ml) and aqueous solution of sodium hydrogencarbonte (500 ml). The separated organic layer was washed with water and brine, dried over magnesium sulfate and treated with activated charcoal. After filtration, the filtrate was evaporated in vacuo. The resulting residue was dissolved in diethyl ether, added ethanol solution of hydrogen chloride, and the resulting precipitate was collected by filtration. The resulting crude compound was recrystallized with ethanol (30 ml). And the resulting crystal was collected by filtration, washed with ethanol and diethyl ether, and dried to give 4,5-bis(4-methoxyphenyl)-2-(N,N-dimethylaminomethyl)thiazole hydrochloride (2.85 g). was refluxed for 2 hours the solvent was evaporated in vacuo the residue was dissolved in chloroform (500 ml) The separated organic layer was washed with water and brine dried over magnesium sulfate treated with activated charcoal After filtration the filtrate was evaporated in vacuo The resulting residue was dissolved in diethyl ether added ethanol solution of hydrogen chloride the resulting precipitate was collected by filtration The resulting crude compound was recrystallized with ethanol (30 ml) And the resulting crystal was collected by filtration washed with ethanol and diethyl ether dried

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

Procedure: A mixture of 118 g. of dimethylaminothioacetamide, 92.4 g. of sodium bicarbonate, 140 g. of 1,3-dichloropropanone and 600 ml. of 1,2-dichloroethane was stirred at ambient temperature for 24 hours, and was then filtered. To the filtrate, at ice-bath temperature, was added 131 g. of thionyl chloride, dropwise. One hundred ml. of additional 1,2-dichloroethane was added, and the mixture was stirred for 2 hours at ambient temperature and then for 1 hour under reflux. The mixture was then chilled overnight, warmed to ambient temperature and filtered. The filter cake was washed with 200 ml. of 1,2-dichloroethane and blown dry, and the solids were dried overnight under vacuum to obtain 202.5 g. of the desired product, substantially identical to the product of Example 5. A mixture of 118 g was then filtered To the filtrate, at ice-bath temperature, was added 131 g of additional 1,2-dichloroethane was added for 1 hour under reflux The mixture was then chilled overnight warmed to ambient temperature filtered The filter cake was washed with 200 ml of 1,2-dichloroethane and blown dry, and the solids were dried overnight under vacuum to obtain 202.5 g

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-(Dimethylamino)ethanethioamide (0.382 g, 3.24 mmol), 1,3-dichloroacetone (0.453 g, 3.56 mmol) and sodium bicarbonate (0.301 g, 3.56 mmol) was stirred in 1,2-dichloroethane (4 mL) at room temperature for 24 h. The reaction mixture was filtered and the filter cake was washed with 1,2-dichloroethane. The filtrate was added dropwise to a cooled (ice bath) solution of thionyl chloride (0.260 mL, 3.56 mmol) in 1,2-dichloroethane (2 mL). The solution was stirred at 70° C. for 0.5 h and then cooled to room temperature. The brown mixture was filtered and washed with 1,2-dichloroethane to afford N-{[4-(chloromethyl)-1,3-thiazol-2-yl]methyl}-N,N-dimethylamine hydrochloride as a brown solid (0.550 g, 2.42 mmol, 75% yield). 1H NMR (400 MHz; D2O): 2.79 (s, 6H); 4.52 (s, 2H); 4.61 (s, 2H); 7.60 (s, 1H). The reaction mixture was filtered the filter cake was washed with 1,2-dichloroethane The filtrate was added dropwise to cooled to room temperature The brown mixture was filtered washed with 1,2-dichloroethane