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Typical Procedure
for the Synthesis of Compounds 3
To a solution of
aminoethanol (2 mmol) in acetone (10 mL) was added anhyd K3PO4 (4
mmol), and the reaction mixture was stirred at r.t. for 30 min.
CS2 (4 mmol) was then added dropwise. The reaction mixture
was stirred for an additional 20 min, and halide (2 mmol) was then
added. Stirring was continued at r.t. until the reaction was completed
(monitored by TLC). The precipitate was filtered and washed with acetone.
The solvent was evaporated under reduced pressure, and the residue
was purified by chromatography on a silica gel column (PE-EtOAc)
to give the desired compounds 3.
Selected Data for Compound 3f
White
solid; mp 104-106 ˚C. ¹H NMR
(300 MHz, CDCl3): δ = 1.83
(s, 6 H), 2.81 (t, J = 7.8
Hz, 2 H), 3.30 (t, J = 8.1
Hz, 2 H), 3.82 (t, J = 6.3
Hz, 2 H), 4.06 (t, J = 6.3
Hz, 2 H), 7.26-7.49 (m, 10 H). MS (EI, 70 eV): m/z (%) = 396
(6) [M]+, 204 (7), 193 (7),
177 (55), 165 (15), 144 (57), 118 (25), 86 (100). Anal. Calcd for
C23H26N2OS2: C, 66.63;
H, 6.10; N, 7.06. Found: C, 66.71; H, 6.10; N, 7.03.
Selected Data for Compound 3h
Light
yellow oil. ¹H NMR (300 MHz, CDCl3): δ = 1.30
(t, J = 7.2
Hz, 3 H), 1.83 (s, 6 H), 3.93 (t, J = 6.3
Hz, 2 H), 4.10 (t, J = 6.3
Hz, 2 H), 4.13 (s 2 H), 4.23 (q, J = 7.2
Hz, 2 H). Anal. Calcd for C10H17NO3S2:
C, 45.60; H, 6.51; N, 5.32. Found: C, 45.45; H, 6.57; N, 5.36.
