Diethyl Sulfate → HCID 19360254, compound

Participants

Reaction Steps

6-Chloro-3-(4-pyridinylamino)benzo[b]thiophene (3 g, 11.5 mmol) was added portionwise as a powder to an ice-cooled suspension of sodium hydride (60% oil dispersion, 0.7 g, 17.5 mmol, washed with heptane) in 25 mL of dimethylformamide. After the anion formation was completed, diethyl sulfate (1.8 g, 11.7 mmol) was added. After one hour the reaction mixture was poured into ice-water and extracted with ether. The organic extract was washed with water and saturated sodium chloride solution, and dried (anhydrous magnesium sulfate), filtered and concentrated to give 5 g of a brown oil. Elution through silica with 10% methanol in ethyl acetate via flash column chromatography yielded 2.3 g of an amber oil. Conversion to the hydrochloride salt in 10% methanol in ether afforded 1.8 g of yellow crystals, mp 288-290°.

Provenance & Evidence