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General Procedure A (for 2b–d,f,g,i,j)
To a suspension of NaH (720 mg, 30 mmol, 3.0 equiv) in DMF
(35 mL), was added a solution of mercaptobenzothiazole (1.7 g,
10 mmol, 1.0 equiv) in DMF (5 mL). The mixture was stirred at
room temperature for 30 min. Alkyl halide (11 mmol, 1.1 equiv)
diluted in DMF (2 mL) was then introduced to the yellow solu-
tion. The reaction was stirred at 70 °C for 3 h, quenched with
water, and extracted with Et2O. The organic layer was washed
five times with brine, dried over MgSO4, filtered, and concen-
trated under reduced pressure. The yellow residue was then
purified by column chromatography on silica gel to afford the
expected compound.
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Med. Chem. Lett. 2004, 14, 187. (c) Dorogov, M. V.; Filimonov, S.
General Procedure B (for 2a,e)
To a solution of Na (rinsed with heptane, 345 mg, 15 mmol, 1.5
equiv) in dry MeOH (dried over CaH2, 30 mL) was slowly added
mercaptobenzothiazole (1.7 g, 10 mmol, 1.0 equiv). The
mixture was stirred at room temperature for 10 min. The alkyl
halide (11 mmol, 1.1 equiv) was then introduced to the yellow
solution. The reaction was stirred at 60 °C for 3 h, quenched
with water, and extracted with CH2Cl2. The organic layer was
washed with brine, dried over MgSO4, filtered, and concen-
© Georg Thieme Verlag Stuttgart · New York — Synlett 2018, 29, A–E