Methanol → methyl (E)-2-(2-dimethylaminomethylidenaminothiazol-4-yl)-2-methoxyiminoacetate

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Reaction Conditions

Reaction Steps

Dimethylaminochloromethyleneammonium chloride (400 mg, 3.1 mmol) was dissolved in 10 ml of tetrahydrofuran, followed by cooling to -3° C. The solution was used with 300 mg (1.5 mmol) of (Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetic acid and the mixture so obtained was stirred for 40 minutes. After the resulting mixture was added with 10 ml of methanol and was then stirred for 10 minutes at room temperature, the mixture was poured into 50 ml of a saturated aqueous solution of sodium hydrogencarbonate. The mixture so obtained was extracted four times with 20 ml portions of chloroform. The extract was dried over anhydrous magnesium sulfate. The dried matter was then concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column, whereby 383 mg of the title compound were obtained (yield: 95%).

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