Dimethylformamide → 4-(2',6'-Dimethylphenoxy)phthalonitrile

HRID 2077141

Reaktionsgleichung

Reaktionsgleichung von HRID 2077141
[N+]([C:4]1[CH:5]=[C:6]([C:12]#[N:13])[C:7](=[CH:10][CH:11]=1)[C:8]#[N:9])([O-])=O.[CH3:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[C:16]=1[OH:22].C([O-])([O-])=O.[K+].[K+].CN(C=O)C>O>[CH3:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[C:16]=1[O:22][C:4]1[CH:5]=[C:6]([C:12]#[N:13])[C:7](=[CH:10][CH:11]=1)[C:8]#[N:9]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 113352,6-DimethylphenolHCID 11430Potassium CarbonateHCID 974431,2-Benzenedicarbonitrile, 4-nitro-

Produkt 1

HCID 9520734-(2',6'-Dimethylphenoxy)phthalonitrileAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of 4-nitro-phthalonitrile (1 eq), 2,6-dimethylphenol (1.2 eq), K2CO3 (2 eq), and DMF (1 mL/mmol 4-nitro-phthalonitrile) was heated under nitrogen at 60° C. for 3 h with stirring After cooling to ambient temperature the mixture was poured into water (6 mL/mL DMF) with stirring. The mixture was extracted twice with EtOAc. The combined organic phases were dried over MgSO4 and concentrated in vacuo. The residue was recrystallized from EtOH to give the title compound as a tan solid (yield: 87%); 1H NMR (CDCl3, 200 MHz): δ=7.70 (d, 1H), 7.05 to 7.16 (m, 5H), 2.08 (s, 6H).

Aufarbeitung

  1. temperatureAfter cooling to ambient temperature the mixture
  2. stirringwith stirring
  3. extractionThe mixture was extracted twice with EtOAc
  4. dry with materialThe combined organic phases were dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was recrystallized from EtOH

Quellen und Nachweise

ORD-Eintrag
ord-cc1e8be18c844e5caeee6bff57f973a3
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07928120B2

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