4-Methyl-3-nitrobenzoic acid → 4-Methyl-N-(3-(2-methyl-1H-imidazole-1-yl)-5-(trifluoromethyl)phenyl)-3-nitrobenzamide
Reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[CH3:13])[C:7]([OH:9])=O)([O-:3])=[O:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[CH3:47][C:48]1[N:49]([C:53]2[CH:54]=[C:55]([CH:57]=[C:58]([C:60]([F:63])([F:62])[F:61])[CH:59]=2)[NH2:56])[CH:50]=[CH:51][N:52]=1>CN(C=O)C.C(OCC)(=O)C>[CH3:13][C:12]1[CH:11]=[CH:10][C:6]([C:7]([NH:56][C:55]2[CH:57]=[C:58]([C:60]([F:61])([F:62])[F:63])[CH:59]=[C:53]([N:49]3[CH:50]=[CH:51][N:52]=[C:48]3[CH3:47])[CH:54]=2)=[O:9])=[CH:5][C:4]=1[N+:1]([O-:3])=[O:2]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
3-Nitro-4-methyl benzoic acid (14.8 g, 81.5 mmol) was dissolved in DMF (150 mL), and HATU (62 g, 163 mmol) and DIPEA (57 mL, 326 mmol) were added thereto at room temperature. The reaction mixture was stirred for 15 minutes, 3-(2-methyl-1H-imidazole-1-yl)-5-(trifluoromethyl)aniline (13.1 g, 54.3 mmol) was added thereto and stirred at 45° C. for 16 hours. The reaction mixture was cooled to room temperature, diluted with ethyl acetate and washed with sat. NaHCO3 solution. The organic layer was dried with anhydrous MgSO4, filtered with Celite and concentrated. The residue was crystallized with ethyl acetate and hexane to obtain the title compound (27 g).
Workup
- customat room temperature
- stirringstirred at 45° C. for 16 hours
- washwashed with sat. NaHCO3 solution
- dry with materialThe organic layer was dried with anhydrous MgSO4
- filtrationfiltered with Celite
- concentrationconcentrated
- customThe residue was crystallized with ethyl acetate and hexane
Sources & evidence
- ORD record
- ord-c673a61c6f9442798b8b33bfafe38f4c
- Source dataset
- uspto-grants-2015_04
- Patent number
- US08999973B2
Reaction notes
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