Cl.CN([CH:5]([SH:7])C)C.C(=O)([O-])[O-].[K+].[K+].F[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1.[CH3:24][N:25]([CH3:28])[CH:26]=O>O>[CH3:24][N:25]([CH3:28])[CH2:26][CH2:5][S:7][C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1To a solution of N,N-dimethylaminoethanethiol hydrochloride (2.9 g, 14 mmol) in N,N-dimethylformamide (DMF) (70 mL) is added potassium carbonate (19 g, 140 mmol), followed by 4-fluoronitrobenzene (1.5 mL, 14 mmol). After stirring overnight at room temperature, the reaction mixture is diluted with water and extracted 3× with ethyl acetate. The combined extracts were washed five times with water and with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude oil is purified by flash chromatography (Isco 40 g Redi-Sep column, MeOH/CHCl3) to give N,N-dimethyl-N-{2-[(4-nitrophenyl)thio]ethyl}amine (2.3 g, 72%) as a golden oil.
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