Nitrogen → 4-(Ethoxymethyl)-2-((4-nitro-2H-1,2,3-triazol-2-yl)methyl)oxazole

HRID 82849Notes

Reaction equation

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

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-(chloromethyl)-4-(ethoxymethyl)oxazole (260 mg, 1.48 mmol) in DMF (4.2 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) (1.76 g of a 9.6% solution in DMF, 1.48 mmol) in DMF (4.2 mL) pre-treated for 30 min with DIPEA (0.51 mL, 2.96 mmol) and the reaction mixture was stirred overnight at 50° C. Water (20 mL), followed by EA (20 mL) was added. The layers were separated and the org. layer was washed with water (3×10 mL), dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (1:1 hept-EA) gave the title compound as a yellow oil: TLC: rf (1:1 hept-EA)=0.40. LC-MS-conditions 07: tR=0.69 min, [M+H]+=254.06.

Workup

additionwas added
customThe layers were separated
washlayer was washed with water (3×10 mL)
dry with materialdried over MgSO4
filtrationfiltered
customthe solvents were removed under reduced pressure
customPurification of the residue by FC (1:1 hept-EA)

Sources & evidence

ORD record: ord-2ccec9eff8a44c5fb80e1d338c9d03e2
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846733B2

Reaction notes

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