Nitrogen → HCID 67958050, compound

HRID 82839Notes

Reaction equation

HRID 82839 reaction equation
N#N.Cl[CH2:4][C:5]1[O:6][CH:7]=[C:8]([CH2:10][O:11][CH3:12])[N:9]=1.[N+:13]([C:16]1[CH:20]=[N:19][NH:18][N:17]=1)([O-:15])=[O:14].CCN(C(C)C)C(C)C>CN(C=O)C.CC(=O)OCC.O>[CH3:12][O:11][CH2:10][C:8]1[N:9]=[C:5]([CH2:4][N:18]2[N:17]=[C:16]([N+:13]([O-:15])=[O:14])[CH:20]=[N:19]2)[O:6][CH:7]=1

Participants

8

Reactant 4

HCID 947NitrogenHCID 81531DiisopropylethylamineHCID 2781504-nitro-2H-1,2,3-triazoleHCID 67958123HCID 67958123, compound

Product 1

HCID 67958050HCID 67958050, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent3×HCID 8857Ethyl AcetateSolvent

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-(methoxymethyl)oxazole (1.38 g, 8.55 mmol) in DMF (24.0 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) (10.16 g of a 9.6% solution in DMF, 8.55 mmol) in DMF (24.0 mL) pre-treated for 30 min with DIPEA (2.93 mL, 17.10 mmol) and the reaction mixture was stirred overnight at 50° C. Water (200 mL), followed by EA (200 mL) was added. The layers were separated and the org. layer was washed with water (3×70 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 a yellow oil: TLC: rf (4:6 hept-EA)=0.38. LC-MS-conditions 07: tR=0.63 min.

Workup

  1. additionwas added
  2. customThe layers were separated
  3. washlayer was washed with water (3×70 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvents were removed under reduced pressure
  7. customPurification of the residue by FC (4:6 hept-EA)

Sources & evidence

ORD record
ord-4597169d33ef4314bb27bf4fcbaf594d
Source dataset
uspto-grants-2014_09
Patent number
US08846733B2

Reaction notes

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