2-Acetylcyclohexanone → (5-Methyl-6,7,8,9-tetrahydro-[1,2,4]triazolo[1,5-a]quinazolin-2-yl)-methanol

HRID 638883Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 638883
[C:1]([CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][C:5]1=O)(=O)[CH3:2].[NH2:11][C:12]1[NH:16][N:15]=[C:14]([CH2:17][OH:18])[N:13]=1>COCCO>[CH3:2][C:1]1[C:4]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[N:16]2[N:15]=[C:14]([CH2:17][OH:18])[N:13]=[C:12]2[N:11]=1

Komponenten

4

Edukt 2

HCID 134002-AcetylcyclohexanoneHCID 178508559HCID 178508559, Verbindung

Produkt 1

HCID 22224538(5-Methyl-6,7,8,9-tetrahydro-[1,2,4]triazolo[1,5-a]quinazolin-2-yl)-methanolAusbeute 50,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80192-MethoxyethanolLösungsmittel

Reaktionsbedingungen

Temperatur
23 °C

Versuchsvorschrift

To a round bottomed flask was loaded 4.2 grams of 2-acetylcyclohexanone, 3.52 grams of (5-Amino-1H-[1,2,4]triazol-3-yl)-methanol and 50 ml 2-methoxyethanol. The mixture was refluxed for 18 hours. Then it was cooled down to 23° C. and concentrated to 5 ml. Then 50 ml ethyl ether was added and the precipitate was filtered and vacuum dried to yielded 3.32 grams of product Yield. 49%. This compound was used directly for the next step. MS: 219.2 (M+H). H-NMR (DMSO): δ 5.49 (t, 1H, OH, J=6 Hz), 4.61 (d, 2H, J=6 Hz), 3.24 (m, 2H), 2.93 (m, 2H), 2.69 (s, 3H), 2.52 (s, 2H), 1.84 (m, 4H).

Aufarbeitung

  1. customTo a round bottomed flask was loaded
  2. temperatureThe mixture was refluxed for 18 hours
  3. concentrationconcentrated to 5 ml
  4. additionThen 50 ml ethyl ether was added
  5. filtrationthe precipitate was filtered
  6. customvacuum dried

Quellen und Nachweise

ORD-Eintrag
ord-9dd6135df5004ceca91ecfd8d7823ffd
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07691842B2

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