Triethylamine → N-(2-azidoethyl)-2,3,4,5,6-pentamethylbenzenesulfonamide

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As in the synthesis of N-(2-azidoethyl)tetradecanamide, 2,3,4,5,6-pentamethylbenzene-1-sulfonyl chloride (0.304 g, 1.23 mmol) was reacted with 2-azidoethanamine (0.106 g, 1.23 mmol) and triethylamine (0.249 g, 2.46 mmol) in dichloromethane (5 mL) to give N-(2-azidoethyl)-2,3,4,5,6-pentamethylbenzenesulfonamide (0.296 g, 81% yield). 1H NMR (300 MHz, CDCl3) δ 5.12 (t, J=3.9 Hz, 1H) δ 3.35 (t, J=5.4 Hz, 2H), δ 3.05 (q, J=6.0, 5.1 Hz, 2H), 2.59 (s, 6H), δ 2.28 (s, 3H), 2.24 (s, 6H) ppm; 13C NMR (75 MHz, CDCl3) δ 139.9, 136.1, 135.2, 134.2, 51.1, 42.3, 19.2, 17.9, 17.3 ppm; HRMS (ESI) calcd for C13H20N4O2S (M+) 296.1307. found 296.1304.

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