2-(4-Isobutylphenyl)propiononitrile → HCID 178440852, Verbindung

HRID 2242924Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2242924
Cl.[NH2:2][OH:3].CC(C)([O-])C.[Na+].[CH2:10]([C:14]1[CH:19]=[CH:18][C:17]([CH:20]([CH3:23])[C:21]#[N:22])=[CH:16][CH:15]=1)[CH:11]([CH3:13])[CH3:12]>C(O)C>[CH2:10]([C:14]1[CH:15]=[CH:16][C:17]([CH:20]([CH3:23])[C:21]([NH:2][OH:3])=[NH:22])=[CH:18][CH:19]=1)[CH:11]([CH3:13])[CH3:12]

Komponenten

5

Edukt 3

HCID 1083742-(4-Isobutylphenyl)propiononitrileHCID 443297Hydroxyamine hydrochlorideHCID 23676156Sodium t-butoxide

Produkt 1

HCID 178440852HCID 178440852, VerbindungAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

A mixture of hydroxylamine hydrochloride (0.38 g, 5.32 mmol) and sodium tert-butoxide (0.5 g, 5.28 mmol) in ethyl alcohol (10 mL) is stirred at r.t. for 15′; the precipitate is filtered off and the mother liquors are added dropwise to a solution of 2-(4-isobutylphenyl)propionitrile (0.11 g, 0.49 mmol) in absolute ethyl alcohol (3 mL). The resulting solution is refluxed 18 h. After cooling at r.t. the solvents are evaporated under reduced pressure and the crude residue is diluted in trichloromethane (25 mL), washed with 5% solution of citric acid (2×15 mL), then with a saturated solution of NaCl (2×15 mL), dried over Na2SO4 and evaporated under vacuum to give 2-(4-isobutylphenyl)-N-hydroxy-propionamidine isolated as white solid after crystallisation from n-hexane (0.075 g, 0.34 mmol). Yield 70%. m.p. 75-78° C. 1H-NMR (CDCl3): δ 7.25 (d, 2H, J=7 Hz); 7.12 (d, 2H, J=7 Hz); 5.030 (bs, 1H, NH); 4.35 (bs, 2H, NH—OH); 3.58 (q, 1H, J=8 Hz); 2.48 (d, 2H, J=8 Hz); 1.87 (m, 1H); 1.50 (d, 3H, J=8 Hz); 0.92 (d, 6H, J=8 Hz).

Aufarbeitung

  1. filtrationthe precipitate is filtered off
  2. temperatureThe resulting solution is refluxed 18 h
  3. temperatureAfter cooling at r.t. the solvents
  4. customare evaporated under reduced pressure
  5. additionthe crude residue is diluted in trichloromethane (25 mL)
  6. washwashed with 5% solution of citric acid (2×15 mL)
  7. dry with materialwith a saturated solution of NaCl (2×15 mL), dried over Na2SO4
  8. customevaporated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-45b6f2ab10d4437c90f3c55c88cbef7e
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07674806B2

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