Diethyl (ethoxymethylene)malonate → Diethyl 2-((2-bromo-4-cyanophenylamino)methylene)malonate

HRID 1484618Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1484618
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[Br:10].C(O[CH:14]=[C:15]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17])C>C1(C)C=CC=CC=1>[Br:10][C:3]1[CH:4]=[C:5]([C:6]#[N:7])[CH:8]=[CH:9][C:2]=1[NH:1][CH:14]=[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:21]([O:23][CH2:24][CH3:25])=[O:22]

Komponenten

4

Edukt 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 15152794-Amino-3-bromobenzonitrile

Produkt 1

HCID 66823182Diethyl 2-((2-bromo-4-cyanophenylamino)methylene)malonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of 5.00 g (25.4 mmol) 4-amino-3-bromobenzonitrile in 30 mL of toluene was added 8.23 g (38.1 mmol) of diethyl ethoxymethylenemalonate (2a). The mixture was then heated to reflux for overnight with a condenser open to the air. The resulting solution was cooled down to room temperature and poured into 100 mL of hexanes. The white precipitate was collected and washed with hexanes (30 mL×3) to yield 11.9 g of an off-while solid as the desired product. MS ESI (m/z) 367 (M+1)+.

Aufarbeitung

  1. temperatureThe mixture was then heated
  2. temperatureto reflux for overnight with a condenser open to the air
  3. customThe white precipitate was collected
  4. washwashed with hexanes (30 mL×3)

Quellen und Nachweise

ORD-Eintrag
ord-ff80e0989fb244b4bcb2492f30de9c67
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09422242B2

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