2-methylsulfanylquinoline synthesis

13synthesis methods

Product Name:2-methylsulfanylquinoline
CAS Number:40279-26-3
Molecular formula:C10H9NS
Molecular Weight:175.25

612-62-4 Synthesis

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Yield:40279-26-3 80%

Reaction Conditions:

in N,N-dimethyl-formamide at 120; for 12 h;Inert atmosphere;Schlenk technique;

Steps:

Preparation of 2-(methylsulfanyl)quinoline (1)

Starting material 1 was prepared according to the method described by Dahaen with a slight modification. A Schlenk tube was charged with 2-chloroquinoline (3.3 g, 20 mmol) and DMF (40 mL). Sodium methanethiolate (90 wt%, 10.3 g, 22 mmol) was added and the resulting mixture was stirred for12 h at 120 °C. The resulting biphasic solution was extracted with Et2O (40 mL × 3). The combinedorganic layer was dried over Na2SO4 and concentrated under a reduced pressure. The resulting residuewas purified by silica gel column chromatography with an eluent (hexane/AcOEt = 20/1) to give 1 (2.8 g,16 mmol, 80%) as a white solid.

References:

Yamagishi, Hiroki;Tsuchiya, Shun;Saito, Hayate;Nogi, Keisuke;Shimokawa, Jun;Yorimitsu, Hideki [Heterocycles,2019,vol. 99,# 1,art. no. A34,p. 301 - 309]