2-Chloroethyl vinyl ether → 4-(Diphenylamino)benzaldehyde N-(Vinyloxyethyl)-N-Phenylhydrazone

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Reaction Steps

A mixture of 4-(diphenylamino)benzaldehyde N-phenylhydrazone (10 g, 0.027 mol) and methyl ethyl ketone (50 ml) was added to 100 ml 3-neck round bottom flask equipped with a reflux condenser and a mechanical stirrer. The mixture was stirred at room temperature until all solid entered into solution. Then, 2-chloroethyl vinyl ether (5.5 ml, 0.054 mol, from Aldrich) was added to the mixture, followed by the addition of potassium hydroxide (3.02 g, 0.054 mol) and potassium carbonate (3.73 g, 0.027 mol) in two portions. The mixture was refluxed for 15 hours. The solvent was evaporated off and the crude product was purified by column chromatography using a mixture of hexane-acetone in a volume ratio of 7:1 as the eluant. Fractions containing the product were collected and the solvents were evaporated. The product was dried at 50° C. in a vacuum oven for 5 hours to yield 3.5 g (38%). The melting point was found to be 107–108° C. The 1H-NMR spectrum (100 MHz) of the product in CDCl3 was characterized by the following chemical shifts (δ, ppm): 3.52–4.47 (m, 6H, N—CH2—CH2—O, CH2═); 6.43 (q, 1H, O—CH═); 6.70–8.03 (m, 20H, Ar, CH═N). The IR spectrum of the product was characterized by the following absorption frequencies (KBr, cm−1): ν(C—H) 2983; 2926; 2878, ν(arene C—H) 3033, ν(C═C, in Ar) 1618; 1591; 1494, ν(C—N) 1315; 1276, γ(Ar) 751; 693. The mass spectrum of the product was characterized by the following mass peaks (m/z): 434.4 (100%, M+1), 148.2.

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