Sulfuric Acid → methyl 6-(benzyloxy)-alpha-methyl-1H-benzotriazole-1-acetate
Reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[N:16]=[N:15][N:14]([CH:17]([CH3:21])[C:18]([OH:20])=[O:19])[C:13]=2[CH:22]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[C:28]([O-])([O-])=O.[K+].[K+]>CO.C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[N:16]=[N:15][N:14]([CH:17]([CH3:21])[C:18]([O:20][CH3:28])=[O:19])[C:13]=2[CH:22]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
6
Procedure
A mixture of 6-(benzyloxy)-α-methyl-1H-benzotriazole-1-acetic acid (36.6 g, 0.123 mole) and concentrated sulfuric acid (2.7 ml) in methanol is stirred at reflux temperature for 6 hours, cooled in an ice bath and treated with K2CO3 (25 g). The resulting mixture is stirred vigorously until a thick slurry results, diluted with methylene chloride and filtered. The filtrate is concentrated in vacuo to give a solid residue. Recrystallization of the residue from methanol affords the title product as a white solid, 27 g, mp 88°-91.5° C., identified by NMR and elemental analyses. Another 4.2 g (81.7% total yield) of the title product is obtained form the mother liquor.
Workup
- temperatureat reflux temperature for 6 hours
- temperaturecooled in an ice bath
- stirringThe resulting mixture is stirred vigorously until a thick slurry
- customresults
- filtrationfiltered
- concentrationThe filtrate is concentrated in vacuo
- customto give a solid residue
- customRecrystallization of the residue from methanol
Sources & evidence
- ORD record
- ord-ddee40dbced442d79b379312ccaef8fa
- Source dataset
- uspto-grants-1994_06
- Patent number
- US05324711
Reaction notes
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