N-bromobutanimide → HCID 68297730, Verbindung

HRID 919899Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 919899
C[O:2][C:3](=O)[CH:4]=[CH:5][C:6](=[C:11]([NH:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][CH:16]=1)[CH3:12])[C:7]([O:9][CH3:10])=[O:8].C[O-].[Na+].[Br:27]N1C(=O)CCC1=O>CO>[CH3:10][O:9][C:7]([C:6]1[CH:5]=[C:4]([Br:27])[C:3](=[O:2])[N:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][CH:16]=2)[C:11]=1[CH3:12])=[O:8]

Komponenten

5

Edukt 3

HCID 67184N-bromobutanimideHCID 10942334Sodium MethoxideHCID 867141454-[1-(4-Cyano-benzylamino)-ethylidene]-pent-2-enedioic acid dimethyl ester

Produkt 1

HCID 68297730HCID 68297730, VerbindungAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

MeOH (90 mL) was added to a flask containing 4-[1-(4-cyano-benzylamino)-ethylidene]-pent-2-enedioic acid dimethyl ester (3.35 g, 10.7 mmol). NaOMe solution (2.44 mL, 10.7 mmol, 4.375 M in MeOH) and N-bromosuccinimide (2.28 g, 12.8 mmol) were added, and the resulting mixture was refluxed for 1 h. After cooling to r.t., the solvent was evaporated in vacuo. Saturated NH4Cl (120 mL) was added, and the resulting mixture was extracted with CH2Cl2. The organic layer was dried over MgSO4 and concentrated. The crude product was chromatographed (0-40% EtOAc/hexanes) to give 2.05 g of the title compound. MS: (+) m/z 361.18, 363.14 (M+Na, 79/81Br).

Aufarbeitung

  1. temperaturethe resulting mixture was refluxed for 1 h
  2. customthe solvent was evaporated in vacuo
  3. additionSaturated NH4Cl (120 mL) was added
  4. extractionthe resulting mixture was extracted with CH2Cl2
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated
  7. customThe crude product was chromatographed (0-40% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-0d3dc784294d44a9ab341530129c8d4d
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09271970B2

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