4-Chloro-3-nitroaniline → N-(4-chloro-3-nitrophenyl)-3-(trifluoromethyl)benzamide
Reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[F:12][C:13]([F:24])([F:23])[C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=1)[C:17](Cl)=[O:18]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:17](=[O:18])[C:16]2[CH:20]=[CH:21][CH:22]=[C:14]([C:13]([F:12])([F:23])[F:24])[CH:15]=2)=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]Participants
5
Procedure
To a solution of 4-chloro-3-nitroaniline (1.72 g, 10.0 mmol) in 60 mL of anhydrous DCM was added crystalline DMAP (1.22 g, 10.0 mmol). The reaction mixture was stirred until all solids dissolved, then 3-trifluoromethylbenzoyl chloride (2.71 g, 13.0 mmol) was added dropwise. The reaction mixture was left to stir at ambient temperature for 6 hrs. The completion of the reaction was monitored by TLC and LC/MS. Then it was transferred into a separatory funnel and washed with water (3×100 mL), saturated NaHCO3 (2×100 mL), brine (1×100 mL), dried over anhydrous Na2SO4 and filtered through a short pad of silica gel. Solvent was removed in vacuo to give the title product as a light-brown solid (3.4 g, 100% yield).
Workup
- dissolutiondissolved
- waitThe reaction mixture was left
- stirringto stir at ambient temperature for 6 hrs
- customThen it was transferred into a separatory funnel
- washwashed with water (3×100 mL), saturated NaHCO3 (2×100 mL), brine (1×100 mL)
- dry with materialdried over anhydrous Na2SO4
- filtrationfiltered through a short pad of silica gel
- customSolvent was removed in vacuo
Sources & evidence
- ORD record
- ord-7b9de41dda7a4053997419ee023dc534
- Source dataset
- uspto-grants-2011_10
- Patent number
- US08030487B2
Reaction notes
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