imidazolidine-2-thione

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

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

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

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

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

Conditions: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 4-(4,6-dimorpholino-1,3,5-triazin-2-yl)aniline (40 mg, 0.12 mmol), imidazolidine-2-thione (15 mg, 0.15 mmol) and mercury(II) chloride (40 mg, 0.15 mmol) in 2 mL of DMF was stirred at 140° C. 16 hr. Then the reaction mixture was cooled to room temperature and filtered through Celite™. The filtration was concentrated and purified by reverse phase chromatography to give N-[4-(4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl)phenyl]-4,5-dihydro-1H-imidazol-2-amine (9.0 mg, 22% yield). HPLC: Rt=1.74 min; MS 411 [M+H]. 16 hr Then the reaction mixture was cooled to room temperature filtered through Celite™ The filtration was concentrated purified by reverse phase chromatography

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

Procedure: A mixture of 3-(bromoacetyl)benzo[b]thiophen-5-carbonitrile (1.05 g), 2-imidazolidinethione (0.4 g), ethanol (31.5 ml), and acetic acid (21 ml) was heated under reflux under nitrogen for 24 hours, then cooled in ice. The resulting precipitate was collected by filtration, washed with ether, and dried in vacuo at 65° C. to give 3-(5,6-dihydroimidazo[2,1-b]thiazol-3-yl)benzo[b]thiophen-5-carbonitrile monohydrobromide as a white solid (1 g), m.p. 303°-305° C. was heated under reflux under nitrogen for 24 hours cooled in ice The resulting precipitate was collected by filtration washed with ether dried in vacuo at 65° C.

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

Procedure: A mixture of the crude 3-(2-bromoacetyl)-5-chlorobenzo[b]thiophen (4.2 g), 2-imidazolidinethione (1 g), ethanol (15 ml) and acetic acid (10 ml) was heated under reflux under nitrogen for 18 hours, then allowed to cool to ambient temperature. The resulting solid was collected by filtration, washed with ethanol (15 ml), and dried in vacuo to give 3-(5-chlorobenzo[b]thiophen-3-yl)-5,6-dihydroimidazo[2,1-b]thiazole monohydrobromide as a white solid (2.1 g), m.p. 286°-288° C. (dec.). was heated under reflux under nitrogen for 18 hours The resulting solid was collected by filtration washed with ethanol (15 ml) dried in vacuo

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

Procedure: A mixture of 3-(2-bromoacetyl)benzo[b]furan (36.9 g), 2-imidazolidinethione (15.75 g), ethanol (600 ml) and acetic acid (400 ml) was heated under reflux for 21 hours then allowed to cool to ambient temperature. The resulting solid was collected by filtration, washed with ether (500 ml), and dissolved in hot methanol (500 ml). Charcoal (2 g) was added and the hot mixture was stirred for a few minutes, then filtered and allowed to cool to ambient temperature. The resulting solid was collected by filtration, ground to a fine powder, and dried in vacuo at 80° C. to give 3-(benzo[b]furan-3-yl)-5,6-dihydroimidazo[2,1-b]thiazole monohydrobromide 0.7 hydrate as an off-white solid (28.1 g), m.p. 251°-254.50C. was heated under reflux for 21 hours The resulting solid was collected by filtration washed with ether (500 ml) dissolved in hot methanol (500 ml) Charcoal (2 g) was added filtered to cool to ambient temperature The resulting solid was collected by filtration, ground to a fine powder dried in vacuo at 80° C.

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

Procedure: A mixture of 3-(2-bromoacetyl)benzo[b]furan (0.25 g), 2-imidazolidinethione (0.11 g), ethanol (30 ml) and acetic acid (20 ml) was heated under reflux for 20 hours, then allowed to cool to ambient temperature. The resulting solid was collected by filtration, washed with ether, and dried in vacuo at ambient temperature to give 3-(benzo[b]furan-3-yl)-5,6-dihydroimidazo[2,1-b]thiazole monohydrobromide monohydrate as a white solid (0.145 g), m.p. 242°-244° C. was heated under reflux for 20 hours The resulting solid was collected by filtration washed with ether dried in vacuo at ambient temperature

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

Procedure: A mixture of 3-(2-bromoacetyl)benzo[b]thiophen (10.0 g), 2-imidazolidinethione (4.0 g), ethanol (120 ml) and acetic acid (80 ml) was heated under reflux for 24 hours then allowed to cool to ambient temperature. The resulting solid was collected by filtration and dried in vacuo at ambient temperature to give 3-(benzo[b]thiophen-3-yl)-5,6-dihydroimidazo[2,1-b]thiazole monohydrobromide 1.8 hydrate as a white solid (11.6 g), m.p. 227°-229° C. was heated under reflux for 24 hours The resulting solid was collected by filtration dried in vacuo at ambient temperature

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

Procedure: A mixture of 3-(2-bromoacetyl)benzo[b]thiophen (2.39 g), 2-imidazolidinethione (0.78 g), ethanol (60 ml) and acetic acid (40 ml) was heated under reflux for 18 hours then allowed to cool to ambient temperature. The resulting solid was collected by filtration, washed with ether (2×50 ml), and dried in vacuo at ambient temperature to give 3-(benzo[b]thiophen-3-yl)-5,6-dihydroimidazo[2,1 -b]thiazole monohydrobromide dihydrate as a white solid (2.96 g), m.p. 239°-240° C. was heated under reflux for 18 hours The resulting solid was collected by filtration washed with ether (2×50 ml) dried in vacuo at ambient temperature