Nitrogen → HCID 67958661, compound

HRID 527247Notes

Reaction equation

N#N.Cl[CH2:4][C:5]1[O:6][CH:7]=[C:8]([C:10]([OH:13])([CH3:12])[CH3:11])[N:9]=1.[N+:14]([C:17]1[CH:21]=[N:20][NH:19][N:18]=1)([O-:16])=[O:15].CCN(C(C)C)C(C)C>CN(C=O)C.CC(=O)OCC.O>[N+:14]([C:17]1[CH:21]=[N:20][N:19]([CH2:4][C:5]2[O:6][CH:7]=[C:8]([C:10]([OH:13])([CH3:12])[CH3:11])[N:9]=2)[N:18]=1)([O-:16])=[O:15]

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 2-(2-(chloromethyl)oxazol-4-yl)propan-2-ol (1.32 g, 7.51 mmol) in DMF (22.0 mL) was added to a solution of 4-nitro-2H-[1,2,3]triazole (T. E. Eagles et al. Organic preparations and procedures 2 (2), 117-119, 1970; P. N. Neuman J. Heterocycl. Chem. 8, 51-56, 1971) (12.84 g of a 8% solution in DMF, 9.01 mmol) in DMF (22.0 mL) pre-treated for 30 min with DIPEA (2.57 mL, 15.01 mmol) and the reaction mixture was stirred overnight at 50° C. Water (60 mL), followed by EA (60 mL) were added. The layers were separated and the org. layer was washed with water (3×60 mL), dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (4:6 hept-EA) gave the title compound as an orange oil: TLC: rf (4:6 hept-EA)=0.30. LC-MS-conditions 06: tR=0.55 min.

Workup

additionwere added
customThe layers were separated
washlayer was washed with water (3×60 mL)
dry with materialdried over MgSO4
filtrationfiltered
customthe solvents were removed under reduced pressure
customPurification of the residue by FC (4:6 hept-EA)

Sources & evidence

ORD record: ord-b876f197eead4286a962fd1deb7c81cf
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346793B2

Reaction notes

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