1H-Benzotriazole-1-carboxaldehyde → {[2-Chloro-3-(trifluoromethyl)phenyl]methyl}formamide
Reaction equation
[Cl:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:12][NH2:13].[CH:14](N1C2C=CC=CC=2N=N1)=[O:15]>O1CCCC1>[Cl:1][C:2]1[C:7]([C:8]([F:10])([F:11])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:12][NH:13][CH:14]=[O:15]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 22 °C
Procedure
A solution of {[2-chloro-3-(trifluoromethyl)phenyl]methyl}amine (1.05 g, 5 mmol) in anhydrous tetrahydrofuran (10 ml) was added dropwise to a solution of N-formyl benzotriazole (0.772 g, 5.25 mmol) in anhydrous tetrahydrofuran (10 ml). The reaction was stirred at 22° C. for 18 hrs then reduced in vacuo and the residue partitioned between dichloromethane (75 ml) and 2N aqueous sodium hydroxide (40 ml). The organic layer was separated and extracted with 2N aqueous sodium hydroxide (40 ml). The organic layer was passed through a hydrophobic frit and reduced in vacuo to give a white solid. The crude product was purified by automated flash silica column chromatography (Biotage SP4), eluting with a solvent gradient of 0-10% ethyl acetate in dichloromethane, to give {[2-chloro-3-(trifluoromethyl)phenyl]methyl}formamide as a white solid.
Workup
- customthe residue partitioned between dichloromethane (75 ml) and 2N aqueous sodium hydroxide (40 ml)
- customThe organic layer was separated
- extractionextracted with 2N aqueous sodium hydroxide (40 ml)
- customto give a white solid
- customThe crude product was purified by automated flash silica column chromatography (Biotage SP4)
- washeluting with a solvent gradient of 0-10% ethyl acetate in dichloromethane
Sources & evidence
- ORD record
- ord-b6b6bc7d043f4a39a83155f795fb250c
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07718693B2
Reaction notes
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