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

HRID 42761

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.[CH3:20][C:21]1([C:26]2[CH:27]=[C:28]([CH:35]=[CH:36][CH:37]=2)[CH2:29]OS(C)(=O)=O)[O:25][CH2:24][CH2:23][O:22]1>CN(C=O)C.CC(=O)OCC.O>[CH3:20][C:21]1([C:26]2[CH:27]=[C:28]([CH:35]=[CH:36][CH:37]=2)[CH2:29][N:8]2[N:7]=[C:6]([N+:3]([O-:5])=[O:4])[CH:10]=[N:9]2)[O:22][CH2:23][CH2:24][O:25]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 (50 mg, 0.43 mmol) in DMF (1.0 mL) was treated with DIPEA (0.15 mL, 0.87 mmol). After 30 min, a solution of methanesulfonic acid 3-(2-methyl-[1,3]dioxolan-2-yl)-benzyl ester (106 mg, 0.52 mmol) in DMF (1.0 mL) was added and the reaction mixture was stirred for 3 days 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 Na2SO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (2:1 hept-EA) gave the title compound as a colorless oil: TLC:rf (1:2 hept-EA)=0.42. LC-MS-conditions 02: tR=0.99 min.

Aufarbeitung

additionwere added
extractionThe aq. layer was extracted with EA (10 mL)
dry with materialextracts were dried over Na2SO4
filtrationfiltered
customthe solvents were removed under reduced pressure
customPurification of the residue by FC (2:1 hept-EA)

Quellen und Nachweise

ORD-Eintrag: ord-5165ea9072ce49c6af505bbc9bc310b2
Quelldatensatz: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08536209B2

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