Nitrogen → 2-((5-(methoxymethyl)furan-2-yl)methyl)-4-nitro-2H-1,2,3-triazole

HRID 82801Notes

Reaction equation

HRID 82801 reaction equation
N#N.[N+:3]([C:6]1[CH:10]=[N:9][N:8]([CH2:11][C:12]2[O:16][C:15]([CH2:17][OH:18])=[CH:14][CH:13]=2)[N:7]=1)([O-:5])=[O:4].[CH3:19]I>C(Cl)Cl>[CH3:19][O:18][CH2:17][C:15]1[O:16][C:12]([CH2:11][N:8]2[N:7]=[C:6]([N+:3]([O-:5])=[O:4])[CH:10]=[N:9]2)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 947NitrogenHCID 6328Methyl iodideHCID 67365277(5-((4-nitro-2H-1,2,3-triazol-2-yl)methyl)furan-2-yl)methanol

Product 1

HCID 679580352-((5-(methoxymethyl)furan-2-yl)methyl)-4-nitro-2H-1,2,3-triazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of (5-((4-nitro-2H-1,2,3-triazol-2-yl)methyl)furan-2-yl)methanol (WO 2009077990A1) (186 mg, 0.83 mmol) in CH2Cl2 (3.0 mL) was added to a suspension of Ag2O (288 mg, 1.24 mmol) and MeI (0.06 mL, 0.99 mmol). The resulting mixture (protected form light) was stirred overnight at 40° C. The reaction mixture was filtered and the solvent was removed under reduced pressure. Purification of the residue by FC (7:3 hept-EA) gave the title compound as a yellow oil: TLC: rf (7:3 hept-EA)=0.27. LC-MS-conditions 07: tR=0.74 min.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent was removed under reduced pressure
  3. customPurification of the residue by FC (7:3 hept-EA)

Sources & evidence

ORD record
ord-569616292ed94a7bbabf1c84837cc584
Source dataset
uspto-grants-2014_09
Patent number
US08846733B2

Reaction notes

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