Dimethyl Sulfate → 3,6-Dimethoxyphthalonitrile

HRID 1489536

Reaktionsgleichung

Reaktionsgleichung von HRID 1489536
S([O:6][CH3:7])(OC)(=O)=O.[C:8](=O)([O-])[O-].[K+].[K+].[C:14]([C:16]1[C:22]([C:23]#[N:24])=[C:21]([OH:25])[CH:20]=[CH:19][C:17]=1O)#[N:15]>CC(=O)CC>[CH3:8][O:25][C:21]1[CH:20]=[CH:19][C:17]([O:6][CH3:7])=[C:16]([C:14]#[N:15])[C:22]=1[C:23]#[N:24]

Komponenten

5

Edukt 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 784672,3-Dicyanohydroquinone

Produkt 1

HCID 3583583,6-Dimethoxyphthalonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6569Methyl Ethyl KetoneLösungsmittel

Versuchsvorschrift

Dimethyl sulfate (15 mL, 0.16 mol) and anhydrous potassium carbonate (24 g, 0.17 mol) are added to a solution of 2,3-dicyanohydroquinone (3.0 g, 0.019 mol) in 100 mL 2-butanone. The reaction mixture is refluxed for 18 hr. under a stream of argon, cooled to room temperature and the resulting solid is collected by filtration. The residue is added to water (100 mL) to dissolve the potassium carbonate and the resulting insoluble material is collected by filtration and dried under vacuum to yield 3.10 g (88%), m.p. 276°-280° C., 1H NMR (DMSO-d6) in ppm, δ=7.63 (s, 2H), 3.93 (s, 6H).

Aufarbeitung

  1. temperatureThe reaction mixture is refluxed for 18 hr
  2. filtrationthe resulting solid is collected by filtration
  3. additionThe residue is added to water (100 mL)
  4. dissolutionto dissolve the potassium carbonate
  5. filtrationthe resulting insoluble material is collected by filtration
  6. customdried under vacuum
  7. customto yield 3.10 g (88%), m.p. 276°-280° C., 1H NMR (DMSO-d6) in ppm, δ=7.63 (s, 2H), 3.93 (s, 6H)

Quellen und Nachweise

ORD-Eintrag
ord-0d1805e881f04a3392b2c13022f9e162
Quelldatensatz
uspto-grants-1997_10
Patentnummer
US05679661

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