m-Chloroperbenzoic acid → 3-(Methoxycarbonyl)-2-methylpyrazine 1-oxide
Reaction equation
[CH3:1][C:2]1[C:3]([C:8]([O:10][CH3:11])=[O:9])=[N:4][CH:5]=[CH:6][N:7]=1.ClC1C=C(C=CC=1)C(OO)=[O:17]>C(Cl)(Cl)Cl>[CH3:11][O:10][C:8]([C:3]1[C:2]([CH3:1])=[N+:7]([O-:17])[CH:6]=[CH:5][N:4]=1)=[O:9]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
In a 1-L flask, the methyl 3-methylpyrazine-2-carboxylate (step 1, 16.08 g, 106 mmol) was suspended in CHCl3 (300 mL). 3-chlorobenzoperoxoic acid (Aldrich, 24.62 g, 143 mmol) was added. The reaction mixture was heated to 70° C. for 16 h. The reaction mixture was quenched with saturated NaHCO3 (200 mL). The layers were separated, and the aqueous layer was further extracted with DCM (2×100 mL). The combined organic layers were dried over MgSO4, and the filtrate was concentrated to afford the title compound. MS m/z=169 [M+H]+. Calculated for C7H8N2O3: 168.
Workup
- customThe reaction mixture was quenched with saturated NaHCO3 (200 mL)
- customThe layers were separated
- extractionthe aqueous layer was further extracted with DCM (2×100 mL)
- dry with materialThe combined organic layers were dried over MgSO4
- concentrationthe filtrate was concentrated
Sources & evidence
- ORD record
- ord-0d3d63765fda4f76a07e41871055090e
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09296734B2
Reaction notes
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