Benzoylhydrazine → HCID 18465756, compound

HRID 1532899Notes

Reaction equation

HRID 1532899 reaction equation
[CH2:1]([O:8][C:9](=[O:12])[CH:10]=[CH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:13]([NH:21][NH2:22])(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(O)(C)C>[C:13]([NH:21][NH:22][CH2:11][CH2:10][C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:12])(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 11955BenzoylhydrazineHCID 75617Benzyl acrylate

Product 1

HCID 18465756HCID 18465756, compoundYield 50.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

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).

Workup

  1. temperatureThe mixture was refluxed for 20 h
  2. concentrationthen concentrated
  3. customThe residue was purified by flash chromatography (20% EtOAc in CH2Cl2)

Sources & evidence

ORD record
ord-3d4e9200c93146499d155c19c387539e
Source dataset
uspto-grants-2001_03
Patent number
US06204261B1

Reaction notes

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