Ethanethiol → HCID 11003284, compound

Participants

Reaction Steps

The AlCl3 (3.6 g, 27 mmol) was stirred in 100 mL of DCE at 0° C., ethanethiol (3 mL, 38 retool) was added, and the mixture stirred for 15 min. The 2-[4-[2-(1-pyrrolidinyl) ethoxy]phenyl]-3- (4-methoxyphenyl) -6-methylpyridine (1.5 g, 3.9 mmol) in 50 mL DCE was added dropwise to the reaction mixture and stirred for 2 h as it was allowed to come to rt, then quenched with 75 mL THF at 0° C., followed by 50 mL 1N HCl and worked up. The crude product was triturated with Et2O, filtered, and dried in vacuo to give 1.3 g (90 % yield) of an off-white solid: mp 159°-161° C.; 1H NMR (CDCl3) d 1.80-184 (bs, 4H, pyrrolidine), 2.61 (s, 3H, pyr-CH3), 2.67-2.69 (bs, 4H, pyrrolidine), 2.93-2.97(m, 2H, CH2N), 4.08-4.10 (m, 2H, OCH2), 6.60-6.65 (m, 4H, ArH), 6.90-6.93 (d, 2H, J=8 Hz, ArH), 7.08-7.11 (d, 1H, J=8 Hz, ArH), 7.23-7.26 (m, 2H, ArH), 7.50-7.53 (d, 1H, J=8 Hz, ArH); MS(FD) 374(M+). Anal. Calcd for C24H26N2O2 : C, 76.98; H, 7.00; N, 7.48. Found: C, 76.70; H, 7.07; N, 7.36.

Provenance & Evidence