Dimethyl Sulfate → methyl 2-fluoro-3-(N-methylbenzamido)benzoate
Reaction equation
[C:1]([NH:9][C:10]1[C:11]([F:20])=[C:12]([CH:17]=[CH:18][CH:19]=1)[C:13]([O:15][CH3:16])=[O:14])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(OC)(O[CH3:25])(=O)=O.[OH-].[K+]>C(#N)C>[F:20][C:11]1[C:10]([N:9]([CH3:25])[C:1](=[O:8])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:19][CH:18]=[CH:17][C:12]=1[C:13]([O:15][CH3:16])=[O:14]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
Methyl 3-benzamido-2-fluorobenzoate (8.75 g, 32.0 mmol) was dissolved in acetonitrile (200 ml). Dimethyl sulfate (4.3 g, 34.1 mmol) and potassium hydroxide (2.63 g, 39.8 mmol) were sequentially added thereto, and the reaction mixture was agitated for 30 minutes at 60° C. The mixture was cooled to room temperature, and then was concentrated. Ethyl acetate was added to the concentration residue, and the mixture was washed with water and dried over anhydrous sodium sulfate. The sodium sulfate was filtered away, and the filtrate was concentrated under reduced pressure. n-hexane was added to the concentration residue, as a result of which 8.00 g (yield: 87%) of the indicated compound was obtained.
Workup
- temperatureThe mixture was cooled to room temperature
- concentrationwas concentrated
- additionEthyl acetate was added to the concentration residue
- washthe mixture was washed with water
- dry with materialdried over anhydrous sodium sulfate
- filtrationThe sodium sulfate was filtered away
- concentrationthe filtrate was concentrated under reduced pressure
- additionn-hexane was added to the concentration residue
Sources & evidence
- ORD record
- ord-9b14133a8b094ab59157ea3479550430
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08853440B2
Reaction notes
Loading…