Molecules 2009, 14
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silica is washed with MeOH and the corresponding thiazolium iodide is recovered after evaporation of
the solvent.
3-(2-Aminophenyl)-2-(heptylthio)-4-methylthiazol-3-ium iodide (2a): Yield: 96% (581 mg, orange
1
solid); mp: 53-55°C; H-NMR (300 MHz, CDCl3) δ = 0.85 (t, 3H, J = 6.7; CH3), 1.25-1.47 (m, 8H;
4(CH2)), 1.77-1.88 (m, 2H; CH2), 2.26-2.27 (d, 3H, J = 1.0; CH3), 3.27-3.59 (m, 2H; SCH2), 4.79 (s,
2H; NH2), 6.79-6.84 ( m, 1H; Ar), 6.93-7.00 (m, 2H; Ar), 7.33-7.38 (m, 1H; Ar), 7.92 (q, 1H, J = 1.0;
=CH); 13C-NMR (75 MHz, CDCl3) δ = 14.12, 14.37, 22.59, 27.62, 28.75, 28.83, 31.47, 36.82, 118.37,
+
118.53, 118.64, 118.83, 126.87, 133.19, 143.16, 145.67, 177.91; HRMS m/z calcd C17H25N2S2 [M-
I]+: 321.1454, found: 321.1455.
3-(2-Aminophenyl-2-(nonylthio)-4-methylthiazol-3-ium iodide (2b): Yield: 96% (617 mg, orange
1
solid); mp: 51-53°C; H-NMR (300 MHz, CDCl3) δ = 0.85 (t, 3H, J = 6.7; CH3), 1.23-1.45 (m, 12H;
6(CH2)), 1.76-1.87 (m, 2H; CH2), 2.26 (d, 3H, J = 0.9; CH3), 3.26-4.11 (m, 4H; SCH2+NH2), 6.78-6.84
( m, 1H; Ar), 6.93-7.00 ( m, 2H; Ar), 7.32-7.38 ( m, 1H; Ar), 7.93 (q, 1H, J = 0.9; =CH); 13C-NMR (75
MHz, CDCl3) δ = 14.18, 14.35, 22.71, 27.62, 28.87, 29.09, 29.23, 29.35, 31.87, 36.81, 118.37, 118.52,
+
118.65, 118.88, 126.86, 133.17, 143.16, 145.65, 177.88; HRMS m/z calcd C19H29N2S2 [M-I]+:
349.1767, found: 349.1767.
3-(2-Aminophenyl)-2-(decylthio)-4-methylthiazol-3-ium iodide (2c): Yield: 94% (622 mg, orange
solid); mp: 52-54 °C; 1H-NMR (300 MHz, CDCl3) δ = 0.85 (t, 3H, J = 6.6; CH3), 1.22-1.44 (m, 14H;
7(CH2)), 1.76-1.86 (m, 2H; CH2), 2.26 (d, 3H, J = 0.7; CH3 ), 3.26-3.58 (m, 2H; SCH2), 4.79 (s, 2H;
NH2), 6.78-6.83 (m, 1H; Ar), 6.93-7.01 (m, 2H; Ar), 7.32-7.37 (m, 1H; Ar), 7.95 (q, 1H, J = 0.7;
13
=CH); C-NMR (75 MHz, CDCl3) δ = 14.17, 14.34, 22.71, 27.60, 28.86, 29.07, 29.31, 29.37, 29.50,
31.90, 36.79, 118.35, 118.50, 118.63, 118.97, 129.85, 133.14, 143.15, 145.59, 177.81; HRMS m/z
+
calcd C20H31N2S2 [M-I]+: 363.1923, found: 363.1922.
3-(2-Aminophenyl)-2-(dodecylthio)-4-methylthiazol-3-ium iodide (2d): Yield: 93% (651 mg, orange
1
solid); mp: 50-52°C; H-NMR (300 MHz, CDCl3) δ = 0.86 (t, 3H, J = 6.7; CH3), 1.23-1.45 (m, 18H;
9(CH2)), 1.77-1.88 (m, 2H; CH2), 2.27 (d, 3H, J = 0.7; CH3), 3.27-3.60 (m, 2H; SCH2), 4.81 (s, 2H;
NH2), 6.79-6.84 (m, 1H; Ar), 6.93-6.99 (m, 2H; Ar), 7.33-7.39 ( m, 1H; Ar), 7.90 (q, 1H, J = 0.7;
13
=CH); C-NMR (75 MHz, CDCl3) δ = 14.22, 14.36, 22.77, 27.64, 28.90, 29.11, 29.41 (2C), 29.59,
29.69 (2C), 31.99, 36.84, 118.37, 118.50, 118.64, 118.81, 126.87, 133.18, 143.20, 145.68, 177.96;
+
HRMS m/z calcd C22H35N2S2 [M-I]+: 391.2236, found: 391.2237.
3-(2-Aminophenyl-2-(octadecylthio)-4-methylthiazol-3-ium iodide (2e): Yield: 98% (797 mg, orange
solid); mp: 51-53 °C; 1H-NMR (300 MHz, CDCl3) δ = 0.86 (t, 3H, J = 6.7; CH3), 1.18-1.46 (m, 30H;
15(CH2)), 1.46-1.78 (m, 2H; CH2), 2.27-2.28 (d, 3H, J = 0.9; CH3), 3.27-3.61 (m, 2H; SCH2), 4.78 (s,
2H; NH2), 6.79-6.85 (m, 1H; Ar), 6.93-6.99 (m, 2H; Ar), 7.34-7.39 (m, 1H; Ar), 7.88 (q, 1H, J = 0.9;
13
=CH); C-NMR (75 MHz, CDCl3) δ = 14.24, 14.40, 22.80, 27.65, 28.92, 29.13, 29.44, 29.48, 29.62,
29.73, 29.77 (brs), 29.81 (brs), 32.04, 36.88, 118.36, 118.54, 118.61 (2C), 126.87, 133.23, 143.17,
+
145.77, 178.05; HRMS m/z calcd C28H47N2S2 [M-I]+: 475.3175, found: 475.3166.