N-bromobutanimide → Ethyl 2-bromo-4-cyano-5-[(2-methylpropyl)amino]benzoate

HRID 906188Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 906188
[C:1]([C:3]1[CH:13]=[CH:12][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][C:4]=1[NH:14][CH2:15][CH:16]([CH3:18])[CH3:17])#[N:2].[Br:19]N1C(=O)CCC1=O>CN(C=O)C.O>[Br:19][C:12]1[CH:13]=[C:3]([C:1]#[N:2])[C:4]([NH:14][CH2:15][CH:16]([CH3:17])[CH3:18])=[CH:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Komponenten

5

Edukt 2

HCID 67184N-bromobutanimideHCID 67405767Ethyl 4-cyano-3-[(2-methylpropylamino)]benzoate

Produkt 1

HCID 67402604Ethyl 2-bromo-4-cyano-5-[(2-methylpropyl)amino]benzoateAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

To a solution of ethyl 4-cyano-3-[(2-methylpropylamino)]benzoate (393 mg, 1.60 mmol) in DMF (10 mL) was added N-bromsuccinimide (284 mg, 1.60 mmol). The mixture was stirred overnight at 45° C. then cooled to room temperature and diluted with water then extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by column chromatography (10% ethyl acetate in hexanes) to give ethyl 2-bromo-4-cyano-5-[(2-methylpropyl)amino]benzoate (374 mg, 72.0%) as a yellow solid. MS (EI) for C14H17BrN2O2: 324 (M+).

Aufarbeitung

  1. temperaturethen cooled to room temperature
  2. extractionthen extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (10% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-2309d0b922894f58a51278575f48ce06
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08012956B2

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