Triethylamine → N-(2-azidoethyl)-5-(dimethylamino)naphthalene-1-sulfonamide

Participants

Reaction Steps

As in the synthesis of N-(2-azidoethyl)tetradecanamide, 5-(dimethylamino)naphthalene-1-sulfonyl chloride (0.321 g, 1.19 mmol) was reacted with 2-azidoethanamine (0.103 g, 1.19 mmol) and triethylamine (0.241 g, 2.38 mmol) in dichloromethane (5 mL) to give N-(2-azidoethyl)-5-(dimethylamino)naphthalene-1-sulfonamide (0.328 g, 86% yield). 1H NMR (300 MHz, CDCl3) δ 8.52 (d, J=8.4 Hz, 1H), δ 8.28 (d, J=8.4 Hz, 1H), δ 8.22 (d, J=0.9 Hz, 1H), δ 7.53 (t, J=8.1 Hz, 1H), δ 7.50 (t, J=7.5 Hz, 1H), δ 7.17 (d, J=7.8 Hz, 1H), δ 5.58 (t, J=1.8 Hz, 1H), δ 3.28 (t, J=5.7 Hz, 2H), δ 3.03 (q, J=6.3, 5.7 Hz, 2H), δ 2.85 (s, 6H) ppm; 13C NMR (75 MHz, CDCl3) δ 152.3, 134.8, 130.9, 130.1, 129.7, 128.9, 123.4, 118.9, 115.6, 51.0, 45.6, 42.6 ppm; HRMS (ESI) calcd for C14H17N5O2S (M+) 319.1103. found 319.1104.

Provenance & Evidence