[N-:1]=[N+:2]=[N-:3].[Na+].CS(O[CH2:10][CH2:11][CH2:12][C:13]1[S:14][CH:15]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:17]=1)(=O)=O>CN(C=O)C.CCOC(C)=O>[N:1]([CH2:10][CH2:11][CH2:12][C:13]1[S:14][CH:15]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:17]=1)=[N+:2]=[N-:3]Sodium azide (263 mg, 4.05 mmol) was added to a solution of 3-(4-phenylthiazol-2-yl)propyl methanesulfonate (0.4 g, 1.35 mmol) in dry DMF (8 mL), and the reaction mixture was heated to 100° C. for 2 h. The mixture was allowed to cool down to room temperature and diluted with EtOAc. The organic product was extracted with EtOAc and the organic layer was washed with H2O and brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure to afford 2-(3-azidopropyl)-4-phenylthiazole (0.3 g, yield 91%) as a pale orange liquid, which was carried through without further purification. 1H NMR (300 MHz, CDCl3) δ 7.91-7.89 (m, 2H), 7.46-7.41 (m, 2H), 7.36-7.31 (m, 2H), 3.49-3.44 (t, J=6.7 Hz, 2H), 3.20-3.15 (t, J=7.5 Hz, 2H), 2.21-2.12 (m, 2H). MS (ESI) m/z: Calculated for C12H12N4S: 244.08. found: 245.2 (M+H)+.
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