Acetic Acid → 2-(1,3-Benzoxazol-2-yl)acetonitrile

HRID 1959795Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1959795
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].C(O)(=O)C.C(#N)[CH:14]([CH2:16][C:17]#[N:18])O>C(O)C.C(Cl)Cl>[O:8]1[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]=[C:14]1[CH2:16][C:17]#[N:18]

Komponenten

6

Edukt 3

HCID 176Acetic AcidHCID 58012-AminophenolHCID 212535622-Hydroxybutanedinitrile

Produkt 1

HCID 8433252-(1,3-Benzoxazol-2-yl)acetonitrileAusbeute 71,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-aminophenol (5.0 g, 45.8 mmol) dissolved in 115 mL of anhydrous ethanol and 8 mL of glacial acetic acid was added malonitrile (9.08 g, 140 mmol) at 100° C. The resulting homogeneous solution was refluxed for 24 hours and the solvent was removed in vacuo to yield a red/brown oil. The oil was diluted with CH2Cl2 (100 mL) and any remaining solids were then removed by filtration. The mother liquor was washed twice with a saturated sodium bicarbonate solution and twice with water, dried over magnesium sulfate, filtered and evaporated to yield 5.2 g (71%) of the product as a yellow oil. This material was used in the subsequent reaction without further purification.

Aufarbeitung

  1. temperatureThe resulting homogeneous solution was refluxed for 24 hours
  2. customthe solvent was removed in vacuo
  3. customto yield a red/brown oil
  4. customany remaining solids were then removed by filtration
  5. washThe mother liquor was washed twice with a saturated sodium bicarbonate solution and twice with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-e3a24efae3d6494282271363baaab33f
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08410272B2

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