Diethyl Ether → 3-(3,5-Dinitrobenzyl)-2-methyl-1,3-benzothiazol-3-ium iodide

Participants

Reaction Steps

2-methylbenzothiazole (3 ml, 20.1 mmol) was dissolved in acetone (25 ml), to which was added 3,5-dinitrobenzyl iodide (7.4 g, 24.1 mmol) and heated with stirring to reflux for 15 hours. The reaction was allowed to cool and added drop-wise to ether (500 ml) to produce a fine yellow solid which was filtered and dried to constant weight in vacuo to give 3-(3,5-dinitrobenzyl)-2-methyl-1,3-benzothiazol-3-ium iodide (5 g, 10.9 mmol, 45% yield). MS: m/z=328 (C15H12N3O4S=330.3). 1H NMR (200 MHz-DMSO-d6): δ 2.85 (s, 1 H); 3.7 (s, 3H); 6.35 (s, 2H); 7.37 (m, 2H); 8.23 (d, 1H); 8.53 (d, 1H); 8.62 (s, 2H): 8.8 (s, 1H).

Provenance & Evidence