S-Methyl methanethiosulfonate → 7-Methylthioimidazo[5,1-b]thiazole

A 1 M ethylmagnesium bromide/THF solution (1.4 ml) was added under ice cooling to a solution of 0.31 g of 7-iodoimidazo[5,1-b]thiazole in 3 ml of dry THF in an argon atmosphere. The mixture was stirred at the same temperature for one hr. Methyl methanethiolsulfonate (0.15 ml) was added thereto. The mixture was stirred at room temperature for 12 hr. A saturated aqueous ammonium chloride solution was added to the reaction solution. Ethyl acetate was added thereto. The mixture was washed with a dilute aqueous sodium thiosulfate solution and saturated brine in that order. The organic layer was dried over anhydrous magnesium sulfate. The solvent was removed by distillation. The residue was purified by column chromatography on silica gel (ethyl acetate) to give 0.15 g of 7-methylthioimidazo[5,1-b]thiazole.

1. stirringThe mixture was stirred at room temperature for 12 hr
2. washThe mixture was washed with a dilute aqueous sodium thiosulfate solution and saturated brine in that order
3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
4. customThe solvent was removed by distillation
5. customThe residue was purified by column chromatography on silica gel (ethyl acetate)

ORD record

ord-9d85925112e74f8287a00bdf46292787

Source dataset

uspto-grants-2002_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06458780B1