Diethyl disulfide → 5-(Ethylthio)pyridin-2-amine

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-bromo-2-(2,2,5,5-tetramethyl-1,2,5-azadisilolidin-1-yl)pyridine (4 g, 12.7 mmol, J. Am. Chem. Soc. 1997, 119, 5499-5511) in tetrahydrofuran (40 mL) was added n-butyllithium at −78° C. under nitrogen. After 2 h, diethyl disulfide (1.7 mL, 12.7 mmol) was added and the mixture was stirred at −78° C. for 3 h. The temperature was gradually raised to room temperature over 2 h. The mixture was poured into ice aqueous sodium hydrogencarbonate. The organic layer was separated and extracted with 2 N hydrochloric acid. The aqueous layer was separated and basified and the mixture was extracted with ethyl acetate (50 mL×4). The organic extracts were dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1 as eluent) to afford the title compound (1.23 g, 63%) as a pale brown solid.

Provenance & Evidence