p-Methoxybenzyl phenyl carbonate

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

Procedure: To 1.3 g (5 mmol) of 2-(5-methyl-2-picolylmercapto)-1H-thieno[3,4-d]imidazole dissolved in 15 ml of anhydrous DMF were added, under nitrogen, 275 mg (6 mmol) of sodium hydride. After the mixture had been heated at 40°-50° C. for 10 min, at room temperature 1.92 g (7.5 mmol) of 4-methoxybenzyl phenyl carbonate (prepared from 4-methoxybenzyl alcohol and phenyl chloroformate) were added, and the mixture was heated at 30°-40° C. for 10 minutes and stirred at room temperature for 1 hour. The solvent was removed by distillation in vacuo, and water was added to the residue. The oily/resinous precipitate was taken up in CH2Cl2, and the solution was dried over MgSO4 and the solvent was evaporated off. The residue crystallized from diethyl ether and was recrystallized from isopropanol. Melting point 120°-121° C. were added, under nitrogen were added the mixture was heated at 30°-40° C. for 10 minutes The solvent was removed by distillation in vacuo, and water was added to the residue the solution was dried over MgSO4 the solvent was evaporated off The residue crystallized from diethyl ether was recrystallized from isopropanol

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

Procedure: To 1.3 g (5 mmol) of 2-(5-methyl-2-picolylmercapto)-1H-thieno[3,4-d]imidazole dissolved in 15 ml of anhydrous DMF were added, under nitrogen, 275 mg (6 mmol) of sodium hydride. After the mixture had been heated at 40°-50° C. for 10 min, at room temperature 1.92 g (7.5 mmol) of 4-methoxybenzyl phenyl carbonate (prepared from 4-methoxybenzyl alcohol and phenyl chloroformate) were added, and the mixture was heated at 30°-40° C. for 10 minutes and stirred at room temperature for 1 hour. The solvent was removed by distillation in vacuo, and water was added to the residue. The oily/resinous precipitate was taken up in CH2Cl2, and the solution was dried over MgSO4 and the solvent was evaporated off. The residue crystallized from diethyl ether and was recrystallized from isopropanol. Melting point 120°-121° C. were added, under nitrogen were added the mixture was heated at 30°-40° C. for 10 minutes The solvent was removed by distillation in vacuo, and water was added to the residue the solution was dried over MgSO4 the solvent was evaporated off The residue crystallized from diethyl ether was recrystallized from isopropanol

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

Procedure: To 1.3 g (5 mmol) of 2-(5-methyl-2-picolylmercapto)-1H-thieno[3,4-d]imidazole dissolved in 15 ml of anhydrous DMF were added, under nitrogen, 275 mg (6 mmol) of sodium hydride. After the mixture had been heated at 40°-50° C. for 10 min, at room temperature 1.92 g (7.5 mmol) of 4-methoxybenzyl phenyl carbonate (prepared from 4-methoxybenzyl alcohol and phenyl chloroformate) were added, and the mixture was heated at 30°-40° C. for 10 minutes and stirred at room temperature for 1 hour. The solvent was removed by distillation in vacuo, and water was added to the residue. The oily/resinous precipitate was taken up in CH2Cl2, and the solution was dried over MgSO4 and the solvent was evaporated off. The residue crystallized from diethyl ether and was recrystallized from isopropanol. Melting point 120°-121° C. were added, under nitrogen were added the mixture was heated at 30°-40° C. for 10 minutes The solvent was removed by distillation in vacuo, and water was added to the residue the solution was dried over MgSO4 the solvent was evaporated off The residue crystallized from diethyl ether was recrystallized from isopropanol