Ethanethiol → HCID 67527990, compound

Temperature

0 °C

To a cooled (0° C.) solution of 0.20 ml (2.6 mmol) of ethanethiol in 7 ml of DMF was added 0.11 g (2.7 mmol) of sodium hydride. The mixture was stirred at 0° C. for 30 min, then 0.50 g, (1.7 mmol) of the title compound from Step A was added. The solution was allowed to stir for 2 h and then quenched with 50 mL of a saturated aqueous sodium bicarbonate solution. The layers were separated and the aqueous phase extracted with ethyl acetate (3×50 mL). The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and evaporated in vacuo to yield the title compound as a light brown solid that was used without further purification. 1H-NMR (500 MHz, CDCl3) δ 4.00 (s, 2H), 2.90 (m, 2H), 2.82 (m, 1H), 2.58 (q, J=7 Hz, 2H), 1.90 (m, 2H), 1.55 (m, 2H), 1.45 (s, 9H), 1.29 (t, J=5 Hz, 3H).

1. stirringto stir for 2 h
2. customquenched with 50 mL of a saturated aqueous sodium bicarbonate solution
3. customThe layers were separated
4. extractionthe aqueous phase extracted with ethyl acetate (3×50 mL)
5. washThe combined organic extracts were washed with brine
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. customevaporated in vacuo

ORD record

ord-8097b0e0b09444e6bcaf967d44e1d0d1

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08354403B2