4-(2,4,6-Trimethylphenyl)-1,3-thiazol-2-amine → (4-Mesitylthiazol-2-yl)(pyridin-4-yl)methanone

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Reaction Steps

To a 0° C. solution of 4-mesitylthiazol-2-amine (7.8 g, 37 mmol)4 in CH2Cl2 (200 mL) was added DMAP (9.0 g, 74 mmol) followed by isonicotinoyl chloride hydrochloride (8.5 g, 48 mmol). Then the mixture was stirred at room temperature for 2 hr. After that, the concentrated mixture was subjected to purification by silica gel chromatography followed by recrystallization from ethanol to give INH41 (10.2 g, 85%) as a white solid; mp 202-203° C. 1H NMR (400 MHz, CDCl3) δ 12.71 (br, 1H), 8.65 (dd, 2H, J=1.6, 4.8 Hz), 7.47 (dd, 2H, J=1.6, 4.8 Hz), 6.79 (s, 1H), 6.54 (s, 2H), 2.15 (s, 3H), 1.87 (s, 6H). 13C NMR (100.5 MHz, CDCl3) δ 164.0, 159.4, 150.2, 148.4, 138.7, 138.0, 136.8, 130.8, 128.5, 121.2, 112.3, 21.1, 20.4. MS (ESI) m/z 324.1 (M+H+), 346.1 (M+Na+). HRMS calculated. for C18H18N3OS (M+H+): 324.1171. found: 324.1167; calculated. for C18H17N3OSNa (M+Na+): 346.0990. found: 346.0984.

Provenance & Evidence