Acetic Acid → 1,1-Dimethylethyl 2-[(4-bromo-2-fluorophenyl)(tetrahydro-3-furanyl)methylidene]hydrazinecarboxylate

HRID 2246615Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2246615
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:10]2[CH2:14][CH2:13][O:12][CH2:11]2)=O)=[C:4]([F:15])[CH:3]=1.[NH:16]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[NH2:17].C(O)(=O)C>CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:10]2[CH2:14][CH2:13][O:12][CH2:11]2)=[N:17][NH:16][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[C:4]([F:15])[CH:3]=1

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 70091tert-Butyl carbazateHCID 58899605(4-Bromo-2-fluorophenyl)(tetrahydro-3-furanyl)methanone2×

Produkt 1

HCID 724574151,1-Dimethylethyl 2-[(4-bromo-2-fluorophenyl)(tetrahydro-3-furanyl)methylidene]hydrazinecarboxylateAusbeute 91,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of ((4-bromo-2-fluorophenyl)(tetrahydro-3-furanyl)methanone (Intermediate 7, 850 mg) 1,1-dimethylethyl hydrazinecarboxylate (616 mg) and acetic acid (1 mL) in methanol (5 mL) was stirred at reflux under nitrogen for 20 h. The solvent was removed under vacuum and the residue was partitioned between ethyl acetate and water. The organic phase was washed with sodium bicarbonate (1M, 10 mL), dried using a hydrophobic filter tube and concentrated under vacuum to give the title compound as a brown oil (1.1 g).

Aufarbeitung

  1. temperatureat reflux under nitrogen for 20 h
  2. customThe solvent was removed under vacuum
  3. customthe residue was partitioned between ethyl acetate and water
  4. washThe organic phase was washed with sodium bicarbonate (1M, 10 mL)
  5. customdried
  6. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-da954334a88e4b0dab79fc4a338c2c1d
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07687532B2

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