Hydrochloric Acid → HCID 441075, compound

Participants

Reaction Conditions

Reaction Steps

NaH (60% in mineral oil, 800 mg, 20.0 mmol, 10.0 equiv) was washed with hexane, dried, and suspended in DMF (20 mL). To this suspension at 0° C. was added ethanethiol (2.96 mL, 40.0 mmol, 20.0 equiv) dropwise over 5 min. The reaction mixture was stirred at 23° C. for 10 min before the addition of quinine (649 mg, 2.00 mmol, 1.00 equiv) in DMF (10 mL) and further stirred for 13 hr at 100° C. The reaction mixture was cooled to 23° C. and neutralized with aqueous 1N HCl. The phases were separated and the aqueous phase was extracted with CH2Cl2 (3×30 mL). The combined organic phases were washed with brine (50 mL) and dried (K2CO3). The filtrate was concentrated in vacuo and the residue was triturated with Et2O to afford 580 mg of the title compound as a colorless solid (93% yield).

Provenance & Evidence