Sodium hydride → 4-[2-(N-Benzoyl-N-methylamino)ethoxy]benzaldehyde

HRID 2260709

Reaction equation

HRID 2260709 reaction equation
[H-].[Na+].[C:3]([N:11]([CH2:13][CH2:14][OH:15])[CH3:12])(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.F[C:17]1[CH:24]=[CH:23][C:20]([CH:21]=[O:22])=[CH:19][CH:18]=1>CN(C)C=O>[C:3]([N:11]([CH2:13][CH2:14][O:15][C:17]1[CH:24]=[CH:23][C:20]([CH:21]=[O:22])=[CH:19][CH:18]=1)[CH3:12])(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 680234-FluorobenzaldehydeHCID 4047264N-(2-hydroxyethyl)-N-methylbenzamide

Product 1

HCID 189988924-[2-(N-Benzoyl-N-methylamino)ethoxy]benzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% dispersion in oil, 1.30 g) was added portionwise to a solution of 2-(N-benzoyl-N-methylamino)ethanol (5.0 g) in dry dimethylformamide (100 ml) at room temperature under a nitrogen atmosphere. The mixture was stirred at room temperature for 1 hour prior to the addition of 4-fluorobenzaldehyde (5.09 g, 4.4 ml), and the mixture then heated at 80° C. for 15 hours. The solvent was evaporated and the residue dissolved in water (500 ml) and extracted with ethyl acetate (3×500 ml). The combined ethyl acetate layers were washed with water (2×300 ml), brine (300 ml), dried (MgSO4) and evaporated to yield an oil. The oil was triturated with hexane, and the residue chromatographed on silica gel with 1.5% methanol in dichloromethane to afford the title compound as an oil.

Workup

  1. temperaturethe mixture then heated at 80° C. for 15 hours
  2. customThe solvent was evaporated
  3. dissolutionthe residue dissolved in water (500 ml)
  4. extractionextracted with ethyl acetate (3×500 ml)
  5. washThe combined ethyl acetate layers were washed with water (2×300 ml), brine (300 ml)
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customto yield an oil
  9. customThe oil was triturated with hexane
  10. customthe residue chromatographed on silica gel with 1.5% methanol in dichloromethane

Sources & evidence

ORD record
ord-db686fe8ffe24339a2419a14a7183478
Source dataset
uspto-grants-1995_12
Patent number
US05478851

Linked notes

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