Methyl iodide → Methyl-benzotriazole-5-carboxylic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH2:6][C:7]2[C:8](=[CH:12][CH:13]=1)[N:9]=[N:10][N:11]=2)=[O:4].[H-].[Na+].CI.[CH3:18]COC(C)=O>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:6]([CH3:18])[C:7]2[C:8](=[CH:12][CH:13]=1)[N:9]=[N:10][N:11]=2)=[O:4]Participants
6
Conditions
- Temperature
- 0 °C
Procedure
1 g of Benzotriazole-5-carboxylic acid methyl ester (5.64 mmol) was dissolved in 20 ml DMF at 0° C. To this solution was added 1 eq. of NaH (60%) at 0° C. The mixture was stirred for 30 min at 0° C., 801 mg (1 eq.) of Methyliodide were slowly added, and the resulting reaction mixture was stirred for 2 h at rt. EtOAc was added and the organic layer was washed extensively with brine and water, dried over MgSO4 and filtered to afford 1 g of crude Methyl-benzotriazole-5-carboxylic acid methyl ester as three different regioisomers. The separation was performed on silica gel using EtOAc/CH 3:7 as eluents.
Workup
- customthe resulting reaction mixture
- stirringwas stirred for 2 h at rt
- washthe organic layer was washed extensively with brine and water
- dry with materialdried over MgSO4
- filtrationfiltered
Sources & evidence
- ORD record
- ord-ad52f87806ef4dc2a4f7808e7473fbb7
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07846925B2
Reaction notes
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