تفاعل #451045

معادلة التفاعل

Benzylacrylate

benzoylhydrazine

→

259

المردود 50.1%

Benzyl 3-(N'-benzoylhydrazino)propanoate

المردود 50.1%

المذيبات

isopropanol

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe mixture was refluxed for 20 h
2. 2
   تركيزthen concentrated
3. 3
   أخرىThe residue was purified by flash chromatography (20% EtOAc in CH2Cl2)

الإجراء التجريبي

Benzylacrylate (1.13 ml, 7.34 mmol) was added to a stirred suspension of benzoylhydrazine (285) (1.0 g, 7.34 mmol) in isopropanol (28 ml). The mixture was refluxed for 20 h, cooled to room temperature then concentrated. The residue was purified by flash chromatography (20% EtOAc in CH2Cl2) to afford 259 (1.098 g, 50%) as an oil which crystallized on standing: mp 65° C.; IR (KBr) 3283, 1723, 1644, 1316, 1201, 1156; 1H NMR (CDCl3) δ 8.32-8.18 (1H, m), 7.81-7.70 (2H, m), 7.57-7.23 (8H, m), 5.36-4.92 (1H, brm), 5.11 (2H, s), 3.26 (2H, t, J=6.5), 2.59 (2H, t, J=6.5); 13C NMR (CDCl3) δ 172.12, 167.27, 135.65, 132.54, 131.66, 128.45, 128.10, 128.06, 126.84, 66.31, 47.33, 33.31; Anal. Calcd for C17H18N2O3 : C, 68.44; H, 6.08; N, 9.39. Found: C, 68.42; H, 6.10; N, 9.38. MS (ES+) 321 (M+Na, 38%), 299 (M+ +1, 100).

المصدر