Hydrochloric Acid → (1Z)-N-(4-Methoxyphenyl)-1-(methylsulfonyl)methanehydrazonoyl chloride

Participants

Reaction Conditions

Reaction Steps

To a solution of p-anisidine (4.39 g, 3.6 mmol) in con. HCl (9.2 mL) and water (20 mL) at 0° C. was slowly added sodium nitrite (2.58 g, 3.7 mmol) in water (20 mL). The reaction mixture was stirred at 0° C. for 0.5 h. The above mixture was poured into a mixture of 3-chloromethanesulphonyl acetone (Grossert, J S, et. al., Can J. Chem. 1984, 62, 798)(6.1 g, 3.5 mmol), acetone (50 mL), sodium acetate (6.7 g, 8.2 mmol), and water (100 mL). The resulting mixture was stirred for 4 h at rt. The precipitate was filtered-off and dried to afford the hydrazone as a red solid (5.28 g, 57%); 1H NMR (CDCl3) δ: 8.05 (s, 1H), 7.12 (d, 2H), 6.91 (d, 2H), 3.80 (s, 3H), 3.23 (s, 3H) ppm.

Provenance & Evidence