Ibuprofenamide → 2-(4-Isobutylphenyl)propiononitrile

HRID 2242922

Reaktionsgleichung

Reaktionsgleichung von HRID 2242922
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH3:15])[C:12]([NH2:14])=O)=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].C(Cl)(Cl)=O.C1(C)C=CC=CC=1>C1(C)C=CC=CC=1.ClC(Cl)Cl>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]([CH3:15])[C:12]#[N:14])=[CH:9][CH:10]=1)[CH:2]([CH3:4])[CH3:3]

Komponenten

4

Edukt 2

HCID 101072IbuprofenamideHCID 19083224Phosgen toluene

Produkt 1

HCID 1083742-(4-Isobutylphenyl)propiononitrileAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 22987606Toluene trichloromethaneLösungsmittel

Versuchsvorschrift

4-isobutyl-α-methylphenylacetamide (2 g; 9.7 mmol), prepared according the procedure described in WO 00/24710, is dissolved in a solution (2:1) toluene/trichloromethane (30 mL). 20% in toluene phosgene (15.5 mL, 30 mmol) is added and the resulting mixture is left stirring 12 h under inert atmosphere until the complete disappearance of the starting reagent. After solvents evaporation under reduced pressure, the crude is dissolved in ethyl acetate (20 mL), the organic phase is washed with a saturated solution of NaHCO3 (2×20 mL) and with a saturated solution of NaCl (2×15 mL), dried over Na2SO4 and evaporated under vacuum to give 2-(4-isobutylphenyl)propionitrile as colourless oil (1.45 g; 7.76 mmol). Yield 80%. 1H-NMR (CDCl3): δ 7.42 (d, 2H, J=7 Hz); 7.28 (d, 2H, J=7 Hz); 4.05 (q, 1H, J=8 Hz); 2.65 (d, 2H, J=8 Hz); 1.95 (m, 1H); 1.80 (d, 3H, J=8 Hz); 1.05 (d, 6H, J=8 Hz).

Aufarbeitung

  1. waitthe resulting mixture is left
  2. customAfter solvents evaporation under reduced pressure
  3. dissolutionthe crude is dissolved in ethyl acetate (20 mL)
  4. washthe organic phase is washed with a saturated solution of NaHCO3 (2×20 mL) and with a saturated solution of NaCl (2×15 mL)
  5. dry with materialdried over Na2SO4
  6. customevaporated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-d4445f8854d54a9997cff64c9f09902d
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07674806B2

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