Nitrogen → 1-[2-(4-Nitro-[1,2,3]triazol-2-ylmethyl)-oxazol-4-yl]-ethanone
Reaktionsgleichung
N#N.[C:3]([C:6]1[N:7]=[C:8]([CH2:11]OS(C)(=O)=O)[O:9][CH:10]=1)(=[O:5])[CH3:4].[N+:17]([C:20]1[CH:24]=[N:23][NH:22][N:21]=1)([O-:19])=[O:18].CCN(C(C)C)C(C)C>CN(C=O)C.CC(=O)OCC.O>[N+:17]([C:20]1[CH:24]=[N:23][N:22]([CH2:11][C:8]2[O:9][CH:10]=[C:6]([C:3](=[O:5])[CH3:4])[N:7]=2)[N:21]=1)([O-:19])=[O:18]Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 3
Reaktionsbedingungen
- Temperatur
- 50 °C
Versuchsvorschrift
In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of methanesulfonic acid 4-acetyl-oxazol-2-ylmethyl ester (116 mg, 0.53 mmol) in DMF (3.0 mL) was added to a solution of 4-nitro-2H-[1,2,3]triazole (62 mg, 0.53 mmol) in DMF (2.0 mL) pre-treated for 30 min with DIPEA (0.20 mL, 1.17 mmol) and the reaction mixture was stirred for 20 h at 50° C. Water (10 mL), followed by EA (10 mL) were added. The aq. layer was extracted with EA (10 mL) and the combined org. extracts were dried over NaSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (3:1 to 1:1 hept-EA) gave the title compound as a yellow solid. TLC:rf (1:2 hept-EA)=0.49. LC-MS-conditions 01: tR=0.76 min.
Aufarbeitung
- additionwere added
- extractionThe aq. layer was extracted with EA (10 mL)
- dry with materialextracts were dried over NaSO4
- filtrationfiltered
- customthe solvents were removed under reduced pressure
- customPurification of the residue by FC (3:1 to 1:1 hept-EA)
Quellen und Nachweise
- ORD-Eintrag
- ord-2f22b333ebb54905ad880f1978174564
- Quelldatensatz
- uspto-grants-2013_11
- Patentnummer
- US08580831B2
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