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

Temperature

-78 °C

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.

1. temperatureThe temperature was gradually raised to room temperature over 2 h
2. additionThe mixture was poured into ice aqueous sodium hydrogencarbonate
3. customThe organic layer was separated
4. extractionextracted with 2 N hydrochloric acid
5. customThe aqueous layer was separated
6. extractionthe mixture was extracted with ethyl acetate (50 mL×4)
7. dry with materialThe organic extracts were dried over sodium sulfate
8. concentrationconcentrated
9. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1 as eluent)

ORD record

ord-ca173668e08248508735d05063ec1071

Source dataset

uspto-grants-2009_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07598393B2