Methane → HCID 69135034, Verbindung

HRID 969510Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 969510
[C:1]([N:4]([C:8]1[C:13]([N+:14]([O-])=O)=[CH:12][C:11]([Br:17])=[CH:10][C:9]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)C(=O)C)(=[O:3])[CH3:2].C.O.NN>CO.[Fe](Cl)(Cl)Cl>[NH2:14][C:13]1[CH:12]=[C:11]([Br:17])[CH:10]=[C:9]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:8]=1[NH:4][C:1](=[O:3])[CH3:2]

Komponenten

6

Edukt 3

HCID 297MethaneHCID 24654Hydrazine hydrate (1:1)HCID 69134269N-Acetyl-N-[4-bromo-2-nitro-6-(phenylmethoxy)phenyl]acetamide

Produkt 1

HCID 69135034HCID 69135034, VerbindungAusbeute 65,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24380Iron chloride (FeCl3)KatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A suspension of 23 g (56 mmol) N-acetyl-N-(2-benzyloxy4-bromo-6-nitro-phenyl)-acetamide, 5.5 g (34 mmol) iron(III) chloride and 13.8 g activated charcoal in 600 ml methanol was heated to reflux. To the reaction mixture were added 28 ml hydrazine hydrate (95%) to maintain gentie reflux. After complete reaction (2 h), the reaction mixture was cooled down and filtered through celite. The filter cake was washed thoroughly with dichloromethane/methanol and the filtrate was evaporated to dryness. The residue was partitioned between dichloromethane/methanol and water. The organic layer was washed with brine, dried over anhydrous magnesium sulphate and evaporated. The residue was recrystallized from boiling ethyl acetate/n-heptane to give 12.3 g (65%) of the title compound as a colourless solid. m.p. 185° C.

Aufarbeitung

  1. temperaturewas heated to reflux
  2. temperatureto maintain gentie
  3. temperaturereflux
  4. customAfter complete reaction (2 h)
  5. temperaturethe reaction mixture was cooled down
  6. filtrationfiltered through celite
  7. washThe filter cake was washed thoroughly with dichloromethane/methanol
  8. customthe filtrate was evaporated to dryness
  9. customThe residue was partitioned between dichloromethane/methanol and water
  10. washThe organic layer was washed with brine
  11. dry with materialdried over anhydrous magnesium sulphate
  12. customevaporated
  13. customThe residue was recrystallized

Quellen und Nachweise

ORD-Eintrag
ord-a39b2eb00b114f41ad10364a6d830536
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07307084B2

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