Water → methyl 3-(N-ethylbenzamido)-2-fluorobenzoate

HRID 534671Notes

Reaction equation

HRID 534671 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.[H-].[Na+].[CH2:23](I)[CH3:24].O>CN(C)C=O>[CH2:23]([N: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])[C:1](=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH3:24]

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 58298651Methyl 3-benzamido-2-fluorobenzoate

Product 1

HCID 58298652methyl 3-(N-ethylbenzamido)-2-fluorobenzoateYield 61.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 3-benzamido-2-fluorobenzoate (3.10 g, 11.0 mmol) was dissolved in N,N-dimethylformamide (30 ml), and the solution was cooled. 60% Sodium hydride (0.53 g, 13.2 mmol) was added thereto, and the reaction mixture was agitated without heating or cooling. 10 minutes later, ethyl iodide (2.05 g, 13.0 mmol) was added to the mixture, and the mixture was agitated overnight at room temperature. Water was added dropwise to the reaction mixture, and the reaction mixture was extracted with ethyl acetate, and dried over anhydrous sodium sulfate. The sodium sulfate was filtered away, and then the filtrate was concentrated under reduced pressure. The concentration residue was purified by silica gel column chromatography (developer solvent: ethyl acetate/n-hexane=1/5), as a result of which 2.03 g (yield: 61%) of the indicated compound was obtained.

Workup

  1. temperaturethe solution was cooled
  2. temperaturewithout heating
  3. temperaturecooling
  4. stirringthe mixture was agitated overnight at room temperature
  5. extractionthe reaction mixture was extracted with ethyl acetate
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationThe sodium sulfate was filtered away
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe concentration residue was purified by silica gel column chromatography (developer solvent: ethyl acetate/n-hexane=1/5)

Sources & evidence

ORD record
ord-62822ae281ea44968493964a42b78f51
Source dataset
uspto-grants-2014_10
Patent number
US08853440B2

Reaction notes

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