[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][NH2:13])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.C(N(CC)CC)C.[C:21](=S)=[S:22].S(Cl)(C1C=CC(C)=CC=1)(=O)=O>C1COCC1>[N:13]([CH2:12][CH2:11][C:5]1[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)=[C:21]=[S:22]
To a solution of 1.0 mL (1.0 g, 5.5 mmol) of 2-(3,5-dimethoxyphenyl)ethanamine (8) in 30 mL of THF was added dropwise 2.5 mL (1.8 g, 18.2 mmol) of triethylamine at 0° C. After stirring for 5 min, a solution of 420 mg (5.52 mmol) of carbon disulfide in 5 mL of THF was added dropwise at 0° C. The resulting solution was slowly warmed to room temperature, stirred for 1.5 h and then cooled to 0° C. To the reaction mixture was added 1.16 g (6.07 mmol) of tosyl chloride in one portion and solution stirred at room temperature for an additional hour. The reaction was quenched by slowly adding 30 mL of saturated NH4Cl(aq). The layers were separated and the aqueous phase was extracted once with ethyl acetate. The combined organic layers were dried (Na2SO4) and concentrated in vacuo. The residue was taken up in methylene chloride and filtered through a plug of silica gel (eluted with methylene chloride) and concentrated in vacuo to afford 1.2 g (100%) of 9 as a colorless oil: 1H NMR (400 MHz, CDCl3) δ 6.37 (s, 3H), 3.80 (s, 6H), 3.71 (t, J=7.0 Hz, 2H), 2.92 (t, J=7.0 Hz, 2H).
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