Nitrogen → 2-((4-(Ethoxymethyl)oxazol-2-yl)methyl)-2H-1,2,3-triazol-4-amine
Reaction equation
N#N.[CH2:3]([O:5][CH2:6][C:7]1[N:8]=[C:9]([CH2:12][N:13]2[N:17]=[C:16]([N+:18]([O-])=O)[CH:15]=[N:14]2)[O:10][CH:11]=1)[CH3:4].[NH4+].[Cl-]>CCO.O.[Fe]>[CH2:3]([O:5][CH2:6][C:7]1[N:8]=[C:9]([CH2:12][N:13]2[N:17]=[C:16]([NH2:18])[CH:15]=[N:14]2)[O:10][CH:11]=1)[CH3:4]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 85 °C
Procedure
In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a mixture of 4-(ethoxymethyl)-2-((4-nitro-2H-1,2,3-triazol-2-yl)methyl)oxazole (115 mg, 0.45 mmol), iron powder (77 mg, 1.36 mmol) and NH4Cl (123 mg, 2.27 mmol) in a mixture of EtOH (2.4 mL) and water (1.2 mL) was stirred at 85° C. for 15 min. The reaction mixture was filtered while hot and concentrated under reduced pressure. CH2Cl2 (25 mL) was added followed by 1N NaOH (25 mL). The layers were separated and the aq. layer was extracted with CH2Cl2 (5×25 mL). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure to give the title compound as a yellow oil. LC-MS-conditions 07: tR=0.48 min; [M+H]+=224.09.
Workup
- filtrationThe reaction mixture was filtered while hot and
- concentrationconcentrated under reduced pressure
- additionCH2Cl2 (25 mL) was added
- customThe layers were separated
- extractionthe aq. layer was extracted with CH2Cl2 (5×25 mL)
- dry with materialextracts were dried over MgSO4
- filtrationfiltered
- customthe solvents were removed under reduced pressure
Sources & evidence
- ORD record
- ord-6f089eded71c4b63b9ac23f3e288e468
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08846733B2
Reaction notes
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