Dimethylformamide → 3-cyano-N, 4-dimethylbenzamide

HRID 1830878

Reaktionsgleichung

I[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:5]([NH:7][CH3:8])=[O:6].[CH3:13][N:14](C=O)C>N.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[C-]#N.[Zn+2].[C-]#N>[C:13]([C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:5]([NH:7][CH3:8])=[O:6])#[N:14]

Komponenten

Reaktionsbedingungen

Temperatur: 120 °C

Versuchsvorschrift

3-Iodo-N, 4-dimethylbenzamide (772 mg), tetrakistriphenylphosphinepalladium (30 mg) and zinc cyanide (250 mg) were suspended in DMF (10 ml) under a nitrogen atmosphere, and the mixture was stirred at 120° C. for 12 hrs. The reaction mixture was diluted with 5% aqueous ammonia-ethyl acetate and the organic layer was washed with water and saturated brine. The organic layer was dried and concentrated, and the residue was subjected to silica gel column chromatography (eluent, hexane:ethyl acetate=2:1–0:1) for purification. The eluate was recrystallized from ethyl acetate-hexane to give the title compound (300 mg) as colorless powder crystals.

Aufarbeitung

washthe organic layer was washed with water and saturated brine
customThe organic layer was dried
concentrationconcentrated
customthe residue was subjected to silica gel column chromatography (eluent, hexane:ethyl acetate=2:1–0:1) for purification
customThe eluate was recrystallized from ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag: ord-16e76a07791f45ecb4f4c029730a3c4b
Quelldatensatz: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07067537B2

Verknüpfte Notizen

Wird geladen…