Dimethylformamide → 3,5-Dimethylbenzonitrile

HRID 426289

Reaktionsgleichung

Reaktionsgleichung von HRID 426289
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH3:11])[CH:10]=1)[C:5]([NH2:7])=O.S(Cl)(Cl)=O.CN(C=O)C.[OH-].[Na+]>C1C=CC=CC=1>[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH3:11])[CH:10]=1)[C:5]#[N:7]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 3194853,5-Dimethylbenzamide

Produkt 1

HCID 897183,5-DimethylbenzonitrileAusbeute 95,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

3,5-dimethylbenzamide (50 g, 0.3356M) was suspended in benzene (400 mL). Thionyl chloride (49 mL, 0.671M) and DMF (2 mL) were added and the mixture was refluxed for 2 hr. After cooling to room temperature, the mixture was poured into a crushed ice. After 1 hr., the solution was neutralized by the addition of 6N sodium hydroxide solution. The product was then extracted with ether, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo to give a yellow solid. The crude product was then purified by silica gel column chromatography (eluent, EA:hexane (1:4)) to afford 42 g (95%) of 3,5-dimethylbenzonitrile as a yellow solid. m.p. 51-52° C. 1H NMR (300 MHz, CDCl3) δ 2.34 (6H, s), 7.21 (1H, s), 7.26 (2H, s).

Aufarbeitung

  1. temperaturethe mixture was refluxed for 2 hr
  2. extractionThe product was then extracted with ether
  3. dry with materialdried with anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customto give a yellow solid
  7. customThe crude product was then purified by silica gel column chromatography (eluent, EA:hexane (1:4))

Quellen und Nachweise

ORD-Eintrag
ord-e3918c5f937746ebab20c95b658a89f3
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08106064B2

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