p-Toluenesulfonic acid → 6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridine-2-carbaldehyde
Reaktionsgleichung
[O:1]1CCO[CH:2]1[C:6]1[N:11]=[C:10]([CH2:12][O:13][N:14]=[C:15]([C:22]2[N:26]([CH3:27])[N:25]=[N:24][N:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:9]=[CH:8][CH:7]=1.CC1C=CC(S(O)(=O)=O)=CC=1>CS(C)=O.O.CCOC(C)=O>[CH3:27][N:26]1[C:22]([C:15](=[N:14][O:13][CH2:12][C:10]2[N:11]=[C:6]([CH:2]=[O:1])[CH:7]=[CH:8][CH:9]=2)[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[N:23][N:24]=[N:25]1Komponenten
6
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 3
Reaktionsbedingungen
- Temperatur
- 100 °C
Versuchsvorschrift
To a solution of N-{[6-(1,3-dioxolan-2-yl)pyridin-2-yl]methoxy}-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine (3.3 g, 9 mmol, 1 eq.) in 75 ml of DMSO and 15 ml of water was added p-TSA (1.79 g, 9.45 mmol, 1.05 eq.). The reaction was heated to 100° C. for 1.5 hrs. After cooling to room temperature, the mixture was diluted with 400 ml of EtOAc, washed with sat. aqueous NaHCO3, followed by water (×2). The organic layer was separated, dried over MgSO4 and concentrated to give 6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridine-2-carbaldehyde (3.1 g, 96% yield) as a viscous yellow oil.
Aufarbeitung
- temperatureAfter cooling to room temperature
- washwashed with sat. aqueous NaHCO3
- customThe organic layer was separated
- dry with materialdried over MgSO4
- concentrationconcentrated
Quellen und Nachweise
- ORD-Eintrag
- ord-31e536262a7041e281c21674b3d64591
- Quelldatensatz
- uspto-grants-2013_06
- Patentnummer
- US08466176B2
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