Hydrochloric Acid → 2,4,5-trifluoro-N-(methylsulfonyl)benzamide
Reaction equation
[F:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([F:12])=[CH:7][C:3]=1[C:4](O)=[O:5].C(N=C=NCCCN(C)C)C.[CH3:24][S:25]([NH2:28])(=[O:27])=[O:26].C(N(CC)CC)C.Cl>CN(C)C1C=CN=CC=1.ClCCl>[F:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([F:12])=[CH:7][C:3]=1[C:4]([NH:28][S:25]([CH3:24])(=[O:27])=[O:26])=[O:5]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
2,4,5-Trifluorobenzoic acid (15 g, 85.2 mmol), 1-ethyl-3-(dimethylaminopropyl)carbodiimide (24.45 g, 128 mmol) and 4-dimethylaminopyridine (15.6 g, 128 mmol) were stirred in dichloromethane at room temperature for 15 minutes under an atmosphere of nitrogen. Methanesulfonamide (12.15 g, 128 mmol) and triethylamine (23.8 g, 254 mmol) were added and the reaction stirred at room temperature overnight. A 1M aqueous solution of hydrogen chloride was added and the mixture was extracted with ethyl acetate. The organic phase was washed sequentially with brine, dried over anhydrous magnesium sulphate, filtered and concentrated in vacuo. The resulting residue was recrystallised from a mixture of ethyl acetate and heptane to afford the title compound (7.8 g, 36%).
Workup
- extractionthe mixture was extracted with ethyl acetate
- washThe organic phase was washed sequentially with brine
- dry with materialdried over anhydrous magnesium sulphate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe resulting residue was recrystallised from a mixture of ethyl acetate and heptane
Sources & evidence
- ORD record
- ord-345345d6325c4939aceb977429fb1a7b
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08685977B2
Reaction notes
Loading…