Diethyl (ethoxymethylene)malonate → Diethyl ({[3-(3,5-dimethyl-4-isoxazolyl)phenyl]amino}methylidene)-propanedioate

HRID 1042976Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1042976
[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9]([CH:11]=[CH:12][CH:13]=2)[NH2:10])=[C:5]([CH3:14])[O:4][N:3]=1.C(O[CH:18]=[C:19]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:20]([O:22][CH2:23][CH3:24])=[O:21])C>>[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9]([NH:10][CH:18]=[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:11]=[CH:12][CH:13]=2)=[C:5]([CH3:14])[O:4][N:3]=1

Komponenten

3

Edukt 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 116870263-(3,5-Dimethyl-isoxazol-4-yl)-phenylamine2×

Produkt 1

HCID 57465569Diethyl ({[3-(3,5-dimethyl-4-isoxazolyl)phenyl]amino}methylidene)-propanedioateAusbeute 52 %

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

3-(3,5-Dimethyl-4-isoxazolyl)aniline (for a preparation see Intermediate 2, 80 g, 420 mmol) and diethyl ethoxymethylenemalonate (92 g, 425 mmol) were mixed together and heated to 130° C. for 20 minutes, liberating ethanol, which was evaporated under reduced pressure. The reaction mixture was poured into iPr2O (1 L) and the resulted precipitate filtered off and washed with iPr2O. The resulting solid was recrystallised from acetonitrile to give the title compound as a brown solid (78 g, 52%).

Aufarbeitung

  1. additionwere mixed together
  2. customliberating ethanol, which was evaporated under reduced pressure
  3. additionThe reaction mixture was poured into iPr2O (1 L)
  4. filtrationthe resulted precipitate filtered off
  5. washwashed with iPr2O
  6. customThe resulting solid was recrystallised from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-8868b3cf06764fb18fba31226de5ad0b
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08557984B2

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