Nitrogen → 5-(4-Nitro-[1,2,3]triazol-2-ylmethyl)-furan-2-carbaldehyde

HRID 42740

Reaction equation

HRID 42740 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]>C(C#N)(C)=O.O=[Mn]=O>[N+:3]([C:6]1[CH:10]=[N:9][N:8]([CH2:11][C:12]2[O:16][C:15]([CH:17]=[O:18])=[CH:14][CH:13]=2)[N:7]=1)([O-:5])=[O:4]

Participants

5

Reactant 2

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

Product 1

HCID 866494765-(4-Nitro-[1,2,3]triazol-2-ylmethyl)-furan-2-carbaldehyde

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 694302-OxopropiononitrileSolvent

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-[1,2,3]triazol-2-ylmethyl)-furan-2-yl]-methanol (248 mg, 1.11 mmol) in AcCN (11.0 mL) was treated at rt with MnO2 (644 mg, 6.67 mmol). The reaction mixture was stirred at rt overnight before being filtered through Celite and the solvent was removed under reduced pressure. Purification of the residue by FC (40:60 hept-EA) gave the title compound: TLC:rf (40:60 hept-EA)=0.26. LC-MS-conditions 02: tR=0.84 min.

Workup

  1. filtrationbefore being filtered through Celite
  2. customthe solvent was removed under reduced pressure
  3. customPurification of the residue by FC (40:60 hept-EA)

Sources & evidence

ORD record
ord-3dcb4a5ff9174205af0466bbdc927706
Source dataset
uspto-grants-2013_09
Patent number
US08536209B2

Linked notes

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