Reaction equation
N#N.[N+:3]([C:6]1[CH:10]=[N:9][NH:8][N:7]=1)([O-:5])=[O:4].[CH3:11][O:12][C:13]([C:15]1[O:16][C:17]([CH2:20]Cl)=[CH:18][CH:19]=1)=[O:14].C([O-])([O-])=O.[K+].[K+].[Br-]>CC(C)=O>[CH3:11][O:12][C:13]([C:15]1[O:16][C:17]([CH2:20][N:8]2[N:7]=[C:6]([N+:3]([O-:5])=[O:4])[CH:10]=[N:9]2)=[CH:18][CH:19]=1)=[O:14]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 4-nitro-2H-[1,2,3]triazole (1.50 g, 13.15 mmol) in acetone (26.3 mL) was treated with 5-chloromethyl-furan-2-carboxylic acid methyl ester (2.66 g, 14.47 mmol) followed by K2CO3 (9.18 g, 65.75 mmol) and TBA bromide (848 mg, 2.63 mmol). The reaction mixture was stirred at rt overnight. The solvent was removed under reduced pressure, water (50 mL) was added and the product was extracted with EA (3×30 mL) and the combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (50:50 hept-EA) gave the title compound as a yellow oil: TLC:rf (50:50 hept-EA)=0.22. LC-MS-conditions 02: tR=0.90 min.
Workup
- customThe solvent was removed under reduced pressure, water (50 mL)
- additionwas added
- extractionthe product was extracted with EA (3×30 mL)
- dry with materialextracts were dried over MgSO4
- filtrationfiltered
- customthe solvents were removed under reduced pressure
- customPurification of the residue by FC (50:50 hept-EA)
Sources & evidence
- ORD record
- ord-6d0d94cd7f044357a20e66c2ebbc202e
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08536209B2
Linked notes
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