Triethylamine → N-[2-methoxy(methyl)amino-2-oxoethyl]-2-(trifluoromethyl)benzamide
Reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:15]=[CH:14][CH:13]=[CH:12][C:4]=1[C:5]([NH:7][CH2:8][C:9]([OH:11])=[O:10])=[O:6].Cl.[CH3:19][NH:20]OC.Cl.[CH3:24]N(C)CCCN=C=NCC.C(N(CC)CC)C>ClCCl.CN(C)C1C=CN=CC=1>[CH3:24][O:10][C:9](=[O:11])[CH:8]([NH:20][CH3:19])[NH:7][C:5](=[O:6])[C:4]1[CH:12]=[CH:13][CH:14]=[CH:15][C:3]=1[C:2]([F:16])([F:17])[F:1]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To 45.2 g of 2-[2-(trifluoromethyl)benzoylamino]acetic acid in 609 ml of dichloromethane, 21.4 g of N,O-dimethylhydroxylamine hydrochloride, 42.0 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 73.8 g of triethylamine and 2.2 g of 4-(dimethylamino)pyridine were added, and the mixture was stirred at room temperature for 18 hours. After completion of the reaction, the reaction mixture was washed with 500 ml of saturated anhydrous sodium hydrogen carbonate, 500 ml of 1N aqueous hydrochloric acid twice and 500 ml of water in this order, the resulting organic layer was dried over saturated aqueous sodium chloride and then anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was washed with 200 ml of hexane to obtain 31.4 g of the desired product as white crystals.
Workup
- customAfter completion of the reaction
- washthe reaction mixture was washed with 500 ml of saturated anhydrous sodium hydrogen carbonate, 500 ml of 1N aqueous hydrochloric acid twice
- dry with material500 ml of water in this order, the resulting organic layer was dried over saturated aqueous sodium chloride
- customanhydrous sodium sulfate, and the solvent was evaporated under reduced pressure
- washThe resulting residue was washed with 200 ml of hexane
Sources & evidence
- ORD record
- ord-fc3ce71d56534995bb824e7f99629d9f
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09434684B2
Reaction notes
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