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

HRID 42749

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

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.

Workup

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)

Sources & evidence

ORD record: ord-21c32ddc19904a78b0953f41777057d9
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536209B2

Linked notes

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