3-(Trifluoromethyl)benzoyl chloride → N-(4-iodo-3-methylphenyl)-3-(trifluoromethyl)benzamide
Reaction equation
[I:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[CH3:9].CCN(C(C)C)C(C)C.[F:19][C:20]([F:31])([F:30])[C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][CH:29]=1)[C:24](Cl)=[O:25]>C(Cl)Cl>[I:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:24](=[O:25])[C:23]2[CH:27]=[CH:28][CH:29]=[C:21]([C:20]([F:19])([F:30])[F:31])[CH:22]=2)=[CH:4][C:3]=1[CH3:9]Participants
5
Procedure
To a solution of 4-iodo-3-methyl aniline (200 mg, 0.86 mmol) and iPr2NEt (0.19 mL, 0.95 mmol) in CH2Cl2 (10 mL) was added 3-(trifluoromethyl)benzoyl chloride (0.133 mL, 0.90 mmol). The mixture was allowed to stir at room temperature for 0.5 h at which time it was diluted with CH2Cl2 (20 mL). The organic layer was washed with aq. HCl (10 mL, 1 M), 9% aq. Na2CO3 (10 mL), brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting oil was used without further purification.
Workup
- washThe organic layer was washed with aq. HCl (10 mL, 1 M), 9% aq. Na2CO3 (10 mL), brine
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe resulting oil was used without further purification
Sources & evidence
- ORD record
- ord-682efe5acc684c7884172e5d2ad5bed8
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07776869B2
Reaction notes
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