Hydroxylamine → 3-[3-(tetrahydro-pyran-2-yloxymethyl)-phenyl]-4H-[1,2,4]oxadiazol-5-one

HRID 1161111Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1161111
N[OH:2].[O:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]1[O:9][CH2:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[C:14]#[N:15].[C:19]([N:26]1C=CN=C1)(N1C=CN=C1)=[O:20].O>C(O)(C)C.O1CCOCC1>[O:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]1[O:9][CH2:10][C:11]1[CH:12]=[C:13]([C:14]2[NH:26][C:19](=[O:20])[O:2][N:15]=2)[CH:16]=[CH:17][CH:18]=1

Komponenten

7

Edukt 4

HCID 787HydroxylamineHCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 219279093-(Tetrahydro-pyran-2-yloxymethyl)-benzonitrile

Produkt 1

HCID 1363488113-[3-(tetrahydro-pyran-2-yloxymethyl)-phenyl]-4H-[1,2,4]oxadiazol-5-oneAusbeute 89,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3776IsopropanolLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Add 50% aqueous hydroxylamine (9.73 g, 147 mmol) dropwise to a refluxing solution of 3-(tetrahydro-pyran-2-yloxymethyl)-benzonitrile (8.00 g, 36.8 mmol) in isopropanol (0.1M). After 2 hours, cool to room temperature and concentrate under reduced pressure to give a residue. Dissolve the residue in dioxane (0.1M). Add carbonyldiimidazole (7.16 g, 44.2 mmol) and heat to 110° C. After 30 minutes, cool to room temperature and pour into water. Extract with ethyl acetate. Combine the organic layers, dry with sodium sulfate, filter and concentrate under reduced pressure to yield the title product as a white solid (9.10 g, 89%): 1H NMR (CDCl3) δ 1.53-1.95 (m, 6H), 3.59 (m, 1H), 3.93 (m, 1H), 4.58 (d, 1H), 4.77 (t, 1H), 4.88 (d, 1H), 7.52 (t, 1H), 7.57 (d, 1H), 7.71 (d, 1H), 7.82 (s, 1H), 11.16 (bs, 1H)

Aufarbeitung

  1. concentrationconcentrate under reduced pressure
  2. customto give a residue
  3. waitAfter 30 minutes
  4. temperaturecool to room temperature
  5. extractionExtract with ethyl acetate
  6. dry with materialdry with sodium sulfate
  7. filtrationfilter
  8. concentrationconcentrate under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-55606058096a4cd58151145fd10f67fb
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07816523B2

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