Trifluoroacetic acid → HCID 23363144, compound
Reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[C:8]([O:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH2:18][N:19]3[CH:23]=[N:22][CH:21]=[N:20]3)[CH:9]=[CH:10][C:5]=2[N:4]=[N:3]1.[N+:24]([O-])([O-:26])=[O:25].[Na+].FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>>[CH3:1][N:2]1[C:6]2[CH:7]=[C:8]([O:11][C:12]3[CH:17]=[CH:16][C:15]([N+:24]([O-:26])=[O:25])=[CH:14][C:13]=3[CH2:18][N:19]3[CH:23]=[N:22][CH:21]=[N:20]3)[CH:9]=[CH:10][C:5]=2[N:4]=[N:3]1Participants
Procedure
The suspension of 1-methyl-6-[2-(1H-1,2,4-triazol-1-ylmethyl)phenoxy]-1H-benzotriazole (0.5 g) from Example 44, sodium nitrate (0.28 g) and trifluoroacetic acid (5 ml) was stirred at room temperature for 3 days. Stirring was done for another day after further addition of sodium nitrate (0.28 g), and the reaction solution was neutralized with sodium hydrogen carbonate solution, prior to extraction in ethyl acetate. The organic layer was washed with saturated sodium chloride solution, and dried over anhydrous sodium sulfate, prior to removal of the solvent under reduced pressure. The resulting crude crystal in pale yellow was washed with ethyl acetate to give white crystal, which was then recrystallized three times for methanol to give the title compound (0.15 g; 25%). The purity of the compound was 98.8% by HPLC.
Workup
- stirringStirring
- waitwas done for another day
- extractionto extraction in ethyl acetate
- washThe organic layer was washed with saturated sodium chloride solution
- dry with materialdried over anhydrous sodium sulfate
- customto removal of the solvent under reduced pressure
- washThe resulting crude crystal in pale yellow was washed with ethyl acetate
- customto give white crystal, which
- customwas then recrystallized three times for methanol
Sources & evidence
- ORD record
- ord-9836934c1f62413e90fb9378563ad918
- Source dataset
- uspto-grants-1996_12
- Patent number
- US05587392
Reaction notes
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