Nitrogen → 2-[5-(2-Methyl-[1,3]dioxolan-2-yl)-furan-2-ylmethyl]-4-nitro-2H-[1,2,3]triazole

HRID 42749

Reaktionsgleichung

N#N.[N+:3]([C:6]1[CH:10]=[N:9][NH:8][N:7]=1)([O-:5])=[O:4].CCN(C(C)C)C(C)C.Cl[CH2:21][C:22]1[O:26][C:25]([C:27]2([CH3:32])[O:31][CH2:30][CH2:29][O:28]2)=[CH:24][CH:23]=1>CN(C=O)C.CC(=O)OCC.O>[CH3:32][C:27]1([C:25]2[O:26][C:22]([CH2:21][N:8]3[N:7]=[C:6]([N+:3]([O-:5])=[O:4])[CH:10]=[N:9]3)=[CH:23][CH:24]=2)[O:28][CH2:29][CH2:30][O:31]1

Komponenten

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 4-nitro-2H-[1,2,3]triazole (875 mg, 7.67 mmol) in DMF (7.0 mL) was treated at rt with DIPEA (2.63 mL, 15.34 mmol). After 30 min, a solution of 2-(5-chloromethyl-furan-2-yl)-2-methyl-[1,3]dioxolane (1.87 g, 9.21 mmol) in DMF (7.0 mL) was added and the reaction mixture was stirred for 16 h at 50° C. Water (100 mL), followed by EA (100 mL) were added. The aq. layer was extracted with EA (100 mL) and the combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (2:1 hept-EA) gave the title compound as an orange oil: TLC:rf (2:1 hept-EA)=0.26. LC-MS-conditions 02: tR=0.95 min; [M+H]+=281.01.

Aufarbeitung

additionwere added
extractionThe aq. layer was extracted with EA (100 mL)
dry with materialextracts were dried over MgSO4
filtrationfiltered
customthe solvents were removed under reduced pressure
customPurification of the residue by FC (2:1 hept-EA)

Quellen und Nachweise

ORD-Eintrag: ord-21c32ddc19904a78b0953f41777057d9
Quelldatensatz: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08536209B2

Verknüpfte Notizen

Wird geladen…