Nitrogen → 2-((5-(methoxymethyl)furan-2-yl)methyl)-2H-1,2,3-triazol-4-amine
Reaction equation
N#N.[CH3:3][O:4][CH2:5][C:6]1[O:10][C:9]([CH2:11][N:12]2[N:16]=[C:15]([N+:17]([O-])=O)[CH:14]=[N:13]2)=[CH:8][CH:7]=1.[NH4+].[Cl-]>CCO.O.[Fe]>[CH3:3][O:4][CH2:5][C:6]1[O:10][C:9]([CH2:11][N:12]2[N:16]=[C:15]([NH2:17])[CH:14]=[N:13]2)=[CH:8][CH:7]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 90 °C
Procedure
In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a mixture of 2-((5-(methoxymethyl)furan-2-yl)methyl)-4-nitro-2H-1,2,3-triazole (97 mg, 0.35 mmol), iron powder (59 mg, 1.04 mmol) and NH4Cl (94 mg, 1.74 mmol) in a mixture of EtOH (1.6 mL) and water (0.8 mL) was stirred at 90° C. for 2 h. The reaction mixture was filtered while hot and concentrated under reduced pressure. CH2Cl2 (20 mL) was added followed by 1N NaOH (10 mL). The layers were separated and the aq. layer was extracted with CH2Cl2 (10 mL). The combined org. extracts were dried over Na2SO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (95:5 CH2Cl2-MeOH) gave the title compound as a yellow oil: TLC: rf (95:5 CH2Cl2-MeOH)=0.39. LC-MS-conditions 07: tR=0.51 min, [M+H]+=209.34.
Workup
- filtrationThe reaction mixture was filtered while hot and
- concentrationconcentrated under reduced pressure
- additionCH2Cl2 (20 mL) was added
- customThe layers were separated
- extractionthe aq. layer was extracted with CH2Cl2 (10 mL)
- dry with materialextracts were dried over Na2SO4
- filtrationfiltered
- customthe solvents were removed under reduced pressure
- customPurification of the residue by FC (95:5 CH2Cl2-MeOH)
Sources & evidence
- ORD record
- ord-f1583d0dbdcc4a6e816c474198fa3169
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08846733B2
Reaction notes
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