2-Chloro-4-trifluoromethylaniline → N-[2-Chloro-4-(trifluoromethyl)phenyl]formamide
Reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:3]=1[NH2:4].N1([CH:22]=[O:23])C2C=CC=CC=2N=N1>O1CCCC1>[Cl:1][C:2]1[CH:8]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:6]=[CH:5][C:3]=1[NH:4][CH:22]=[O:23]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
To a solution of 2-chloro-4-(trifluoromethyl)aniline (500 mg, 2.56 mmol) in tetrahydrofuran (THF) (8 mL) was added 1H-1,2,3-benzotriazole-1-carbaldehyde (489 mg, 3.32 mmol, Sigma-Aldrich). The reaction mixture was heated to 70° C. and stirred for 18 hours. To the reaction mixture was added 1H-1,2,3-benzotriazole-1-carbaldehyde (1.16 mmol, 245 mg) and the reaction mixture heated to 70° C. for a further 5 hours. The reaction mixture was concentrated under vacuum and the residue partitioned between DCM (20 mL) and 2N HCl (10 mL). The organic layer was collected via a hydrophobic frit and the solvent removed under vacuum.
Workup
- temperaturethe reaction mixture heated to 70° C. for a further 5 hours
- concentrationThe reaction mixture was concentrated under vacuum
- customthe residue partitioned between DCM (20 mL) and 2N HCl (10 mL)
- customThe organic layer was collected via a hydrophobic frit
- customthe solvent removed under vacuum
Sources & evidence
- ORD record
- ord-dca2237f19924106b45987aad09a626a
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09115132B2
Reaction notes
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