Triethylamine → 4-(3'-Methylanilino)-6-methylthiomethylquinazoline

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Reaction Steps

Sodium methanethiolate (0.141 g) was added to a stirred mixture of 6-bromomethyl-4-(3'-methylanilino)quinazoline (0.6 g), triethylamine (0.203 g) and DMF (2 ml). The mixture was stirred at ambient temperature for 4 hours. The mixture was evaporated and the residue was purified by column chromatography using increasingly polar mixtures of methylene chloride and ethyl acetate as eluent. There was thus obtained an oil which was triturated under a mixture of hexane and diethyl ether to give 4-(3'-methylanilino)-6-methylthiomethylquinazoline (0.205 g), m.p. 134°-136° C. NMR Spectrum: (CD3SOCD3) 2.01 (s, 3H), 2.34 (s, 3H), 3.88 (s, 2H), 6.97 (d, 1H), 7.28 (t, 1H), 7.6 (m, 2H), 7.75 (d, 1H), 7.83 (m, 1H), 8.45 (d, 1H), 8.58 (s, 1H), 9.8 (broad s, 1H); Elemental Analysis: Found C, 69.7; H, 5.8; N, 14.21 C17H17N3S. 0.1C6H14 requires C, 69.5; H, 6.1; N, 13.8%.

Provenance & Evidence