Hydrazinecarboxamide,2-[1-(3-chlorophenyl)ethylidene]- synthesis

Yield:14760-30-6 85%

Reaction Conditions:

Stage #1: semicarbazide hydrochloridewith sodium acetate in ethanol at 20; for 0.25 h;
Stage #2: 3'-Chloroacetophenone in ethanol at 20;

Steps:

5 4.2. General procedure for the preparation of semicarbazones 3a-k

General procedure: To a solution of semicarbazide hydrochloride 4 (2.5mmol) in EtOH (10mL), sodium acetate was added (2.5mmol) and the reaction mixture was stirred for 15min at room temperature. Then, aldehyde or ketone 5 (2.5mmol) was added to the mixture and stirred overnight at room temperature. A solid precipitated and it was vacuum filtered, washed with EtOH, then with H₂O and finally vacuum dried. 4.2.5
m-Chlorophenylethanone semicarbazone (3e)
Yield 85%, solid, ¹H NMR (DMSO-d₆) δ 2.17 (s, 3H), 6.61 (bs, 2H), 7.38 (dd, J = 1.3, 4.0 Hz, 1H), 7.74-7.79 (m, 1H), 7.93 (d, J = 0.7 Hz, 1H), 9.45 (s, 1H); ¹³C NMR (DMSO-d₆) δ 13.3, 124.7, 125.6, 128.2, 130.0, 133.3, 140.4, 142.5, 157.2; HRMS calcd for C₉H₁₀ClN₃ONa [M+Na]⁺ 234.0512, found 234.0462.

References:

Pizzo, Chiara;Faral-Tello, Paula;Yaluff, Gloria;Serna, Elva;Torres, Susana;Vera, Ninfa;Saiz, Cecilia;Robello, Carlos;Mahler, Graciela [European Journal of Medicinal Chemistry,2016,vol. 109,p. 107 - 113]