Formaldehyde → 4-Diethylaminobenzaldehyde N-2,3-epoxvpropyl-N-phenylhydrazone

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Reaction Steps

4-(Diethylamino)benzaldehyde N-2,3-epoxypropyl-N-phenylhydrazone was prepared according to the preparation procedure above for 9-ethyl-3-carbazolecarboxaldehyde N-2,3-epoxypropyl-N-phenylhydrazone except that 9-ethyl-3-carbazolecarboxaldehyde phenylhydrazone was replaced by 4-(diethylamino)benzaldehyde phenylhydrazone and the product was recrystallized from diethyl ether. The yield of 4-(diethylamino)benzaldehyde N-2,3-epoxypropyl-N-phenylhydrazone was 69%. The product had a melting point of 79–80.5° C. when recrystallized from diethyl ether. A 1H-NMR spectrum was obtained in CDCl3 with the following results (δ in ppm, 250 MHz): δ=7.7–6.7 (m, 8H, Ar, CH═N); δ=6.6 (d, 2H, 2-H, 6-H of p-Ph); δ=4.4–3.6 (m, 2H, NCH2CH); δ=3.6–3.0 (m, 5H, CH2CH3, CH2CHCH2); δ=2.75 (m, 1H, ABX, cis-HA of CH2O); δ=2.55 (m, ABX, trans-HB of CH2O); δ=1.1 (t, J=7.0 Hz, 6H, CH3). An elemental analysis found the following weight percents of the elements: C, 74.45; H, 7.84; N, 12.72, which compares with the following calculated elemental weight percent for a compound with the formula C20H25N3O of: C, 74.27; H, 7.79; N, 12.99.

Provenance & Evidence