1-methylimidazolidine-2-thione

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

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

Procedure: To a suspension of 1-methylimidazolidine-2-thione (5.17 g, 44.5 mmol) in acetone (50 mL) was added MeI (2.9 mL, 46.6 mmol). The solution was allowed to stir at room temperature for 4 h and the resulting solid was quickly filtered and then dried in vacuo to give 1-methyl-2-(methylthio)-4,5-dihydro-1H-imidazole hydroiodide (8.79 g, 77%) as beige solid. the resulting solid was quickly filtered dried in vacuo

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

Procedure: A solution of 12.7 g of iodine and 25 g of potassium iodide in 100 ml of water is added dropwise to a mixture of 7.25 g of 1,2-dimethylindole in 60 ml methanol and 5.8 g of 1-methyl-2-imidazolidinethione in 100 ml methanol. The reaction mixture is stirred for 2 hours at room temperature. The crystalline precipitate formed was filtered and recrystallized from a mixture of methanol, ethyl acetate and ether to yield 1,2 -dimethyl-3-(1-methyl-2-imidazolin-2-ylthio)-indole hydriodide which melts at 250°-251° (with decomposition). The crystalline precipitate formed was filtered recrystallized from a mixture of methanol, ethyl acetate and ether

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

Procedure: A mixture of 5.85 g indole in 50 ml methanol and 5.8 g 1-methyl-2-imidazolidinethione in 100 ml methanol is treated with a solution of 12.7 g of iodine and 25 g potassium iodide in 100 ml water. The mixture is stirred for 2 hours at room temperature, the clear solution is concentrated in vacuo to one third of the original volume and cooled. The solid which separates is filtered off and recrystallized from a mixture of methanol and ethyl acetate to give 3-(1-methyl-2-imidazolin-2-ylthio)-indole hydriodide melting at 215°-216°. the clear solution is concentrated in vacuo to one third of the original volume cooled The solid which separates is filtered off recrystallized from a mixture of methanol and ethyl acetate

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

Procedure: A mixture of 5.85 g indole in 50 ml methanol and 5.8 g 1-methyl-2-imidazolidinethione in 100 ml methanol is treated with a solution of 12.7 g of iodine and 25 g potassium iodide in 100 ml water. The mixture is stirred for 2 hours at room temperature, the clear solution is concentrated in vacuo to one third of the original volume and cooled. The solid which separates is filtered off and recrystallized from a mixture of methanol and ethyl acetate to give 3-(1-methyl-2-imidazolin-2-ylthio)-indole hydriodide melting at 215°-216°. the clear solution is concentrated in vacuo to one third of the original volume cooled The solid which separates is filtered off recrystallized from a mixture of methanol and ethyl acetate

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

Procedure: A solution of 12.7 g of iodine and 25 g of potassium iodide in 100 ml of water is added dropwise to a mixture of 7.25 g of 1,2-dimethylindole in 60 ml methanol and 5.8 g of 1-methyl-2-imidazolidinethione in 100 ml methanol. The reaction mixture is stirred for 2 hours at room temperature. The crystalline precipitate formed was filtered and recrystallized from a mixture of methanol, ethyl acetate and ether to yield 1,2-dimethyl-3-(1-methyl-2-imidazolin-2-ylthio)-indole hydriodide which melts at 250°-251° (with decomposition). The crystalline precipitate formed was filtered recrystallized from a mixture of methanol, ethyl acetate and ether

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

Procedure: A mixture of 5.85 g indole in 50 ml methanol and 5.8 g 1-methyl-2-imidazolidinethione in 100 ml methanol is treated with a solution of 12.7 g of iodine and 25 g potassium iodide in 100 ml water. The mixture is stirred for 2 hours at room temperature, the clear solution is concentrated in vacuo to one third of the original volume and cooled. The solid which separates is filtered off and recrystallized from a mixture of methanol and ethyl acetate to give 3-(1-methyl-2-imidazolin-2-ylthio)-indole hydriodide melting at 215°-216°. the clear solution is concentrated in vacuo to one third of the original volume cooled The solid which separates is filtered off recrystallized from a mixture of methanol and ethyl acetate

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

Procedure: A mixture of 5.85 g indole in 50 ml methanol and 5.8 g 1-methyl-2-imidazolidinethione in 100 ml methanol is treated with a solution of 12.7 g of iodine and 25 g potassium iodide in 100 ml water. The mixture is stirred for 2 hours at room temperature, the clear solution is concentrated in vacuo to one third of the original volume and cooled. The solid which separates is filtered off and recrystallized from a mixture of methanol and ethyl acetate to give 3-(1-methyl-2-imidazolin-2-ylthio)-indole hydriodide melting at 215°-216°. the clear solution is concentrated in vacuo to one third of the original volume cooled The solid which separates is filtered off recrystallized from a mixture of methanol and ethyl acetate

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

Procedure: Essentially the procedure of Example 37 was used, but starting with (5R)-3-(4-(3,6-dihydro-2H-pyran-4-yl)-3-fluorophenyl)-5-methanesulfonyloxymethyloxazolidin-2-one (300 mg, 0.81 mM), and 1-methylimidazolidin-2-thione (100 mg, 0.88 mM) and heating the reaction at 60° for 1.5 hours. Chromatography on two columns gave the desired product (29 mg). heating the reaction at 60° for 1.5 hours

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

Procedure: To a suspension of 1-methylimidazolidine-2-thione (5.17 g, 44.5 mmol) in acetone (50 mL) was added MeI (2.9 mL, 46.6 mmol). The solution was allowed to stir at room temperature for 4 h and the resulting solid was quickly filtered and then dried in vacuo to give 1-methyl-2-(methylthio)-4,5-dihydro-1H-imidazole hydroiodide (8.79 g, 77%) as beige solid. the resulting solid was quickly filtered dried in vacuo

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

Procedure: To a suspension of 1-methylimidazolidine-2-thione (5.17 g, 44.5 mmol) in acetone (50 mL) was added MeI (2.9 mL, 46.6 mmol). The solution was allowed to stir at room temperature for 4 h and the resulting solid was quickly filtered and then dried in vacuo to give 1-methyl-2-(methylthio)-4,5-dihydro-1H-imidazole hydroiodide (8.79 g, 77%) as beige solid. the resulting solid was quickly filtered dried in vacuo

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

Procedure: To a suspension of 1-methylimidazolidine-2-thione (5.17 g, 44.5 mmol) in acetone (50 mL) was added MeI (2.9 mL, 46.6 mmol). The solution was allowed to stir at room temperature for 4 h and the resulting solid was quickly filtered and then dried in vacuo to give 1-methyl-2-(methylthio)-4,5-dihydro-1H-imidazole hydroiodide (8.79 g, 77%) as beige solid. the resulting solid was quickly filtered dried in vacuo