4-Hydroxybenzoic acid hydrazide → 4-Hydroxy-benzoic acid (5-ethyl-furan-2-ylmethylene)-hydrazide

HRID 1667562

Reaktionsgleichung

Reaktionsgleichung von HRID 1667562
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][NH2:9])=[O:7])=[CH:4][CH:3]=1.[CH2:12]([C:14]1[O:18][C:17]([CH:19]=O)=[CH:16][CH:15]=1)[CH3:13]>C(O)(=O)C.CCO>[CH2:12]([C:14]1[O:18][C:17]([CH:19]=[N:9][NH:8][C:6](=[O:7])[C:5]2[CH:10]=[CH:11][C:2]([OH:1])=[CH:3][CH:4]=2)=[CH:16][CH:15]=1)[CH3:13]

Komponenten

5

Edukt 2

HCID 17424-Hydroxybenzoic acid hydrazideHCID 899895-Ethyl-2-furaldehyde

Produkt 1

HCID 674437884-Hydroxy-benzoic acid (5-ethyl-furan-2-ylmethylene)-hydrazideAusbeute 85,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 4-hydroxy-benzoic acid hydrazide (0.3 g, 0.002 mol) and 5-ethyl-2-furaldehyde (0.25 g, 0.002 mol) in abs. EtOH (10 mL), was added 1 drop of acetic acid. The reaction mixture was refluxed for 5 hours. The reaction mixture was cooling to room temperature and concentrated to remove solvent. The resulting residue was solidified by pet ether to give red solid 0.44 g, in 85% yield, mp: 60.5° C. 1H NMR (DMSO-d6) δ 11.53 (s, 1H), 10.16 (s, 1H), 8.24 (s, 1H), 7.79 (d, 2H), 6.87 (d, 2H), 6.81 (s, 1H), 2.71 (q, 2H), 1.24 (t, 3H). 13C NMR (DMSO-d6) δ164.5, 162.1, 161.2, 149.8, 138.5, 131.5, 125.7, 116.9, 116.7, 108.9, 22.8, 13.8. Anal. Calcd for C14H14N2O3: C, 65.11; H, 5.46; N, 10.85. Found: C, 65.00; H, 5.36; N, 10.55.

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 5 hours
  2. concentrationconcentrated
  3. customto remove solvent

Quellen und Nachweise

ORD-Eintrag
ord-b0a1696aa0d44c688404799d5e6795f2
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08044241B2

Verknüpfte Notizen

Wird geladen…