Acetophenone → Acetophenone benzoylhydrazone

HRID 1655653

Reaktionsgleichung

Reaktionsgleichung von HRID 1655653
[C:1]([NH:9][NH2:10])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=O)[CH3:12]>O1CCCC1.Cl>[C:1]([NH:9][N:10]=[C:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH3:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 7410AcetophenoneHCID 11955Benzoylhydrazine

Produkt 1

HCID 346107Acetophenone benzoylhydrazone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a solution of benzoic acid hydrazide (5.70 g, 0.042 mol) in tetrahydrofuran (75 mL) was added acetophenone (5.5 g, 0.046 mol) followed by concentrated HCl (3 drops). The reaction was allowed to stir for 12 h at 25° C. during which time the product precipitated as a colorless crystalline solid. The product was filtered, washed with tetrahydrofuran (1×30 mL), diethyl ether (3×60 mL) and pentane (2×60 mL), and the crystalline solids were dried in vacuo (6.65 g, 64%). 1H NMR (CD2Cl2): δ 2.35 (s, 3H, CH3), 7.30-8.0 (m, 10H, Ph), 9.0 (br, 1H, NH). All other substrates were prepared in a similar fashion.

Aufarbeitung

  1. customprecipitated as a colorless crystalline solid
  2. filtrationThe product was filtered
  3. washwashed with tetrahydrofuran (1×30 mL), diethyl ether (3×60 mL) and pentane (2×60 mL)
  4. customthe crystalline solids were dried in vacuo (6.65 g, 64%)
  5. customAll other substrates were prepared in a similar fashion

Quellen und Nachweise

ORD-Eintrag
ord-a33879457e694c5c93d83a4fcca716df
Quelldatensatz
uspto-grants-1993_10
Patentnummer
US05250731

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