Ethyl benzoate → N-(2-hydroxyethyl)-N-methylbenzamide

HRID 2260708Notes

Reaction equation

HRID 2260708 reaction equation
[C:1]([O:9]CC)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:12][NH:13][CH2:14][CH2:15][OH:16]>O>[C:1]([N:13]([CH2:14][CH2:15][OH:16])[CH3:12])(=[O:9])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 7165Ethyl benzoateHCID 80162-(Methylamino)ethanol

Product 1

HCID 4047264N-(2-hydroxyethyl)-N-methylbenzamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl benzoate (16.0 g, 15.3 ml) was dissolved in 2-(N-methylamino)ethanol (200 ml) and the mixture heated at reflux for 17.5 hours, cooled and diluted with water (1 l). The mixture was extracted with dichloromethane (4×200 ml), and the combined dichloromethane solutions washed with brine (300 ml), dried (MgSO4) and evaporated. The title compound, an oil, was used without further purification.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 17.5 hours
  3. temperaturecooled
  4. extractionThe mixture was extracted with dichloromethane (4×200 ml)
  5. washthe combined dichloromethane solutions washed with brine (300 ml)
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe title compound, an oil, was used without further purification

Sources & evidence

ORD record
ord-b1e3069bf01a4dadac9d2d81c0cd3018
Source dataset
uspto-grants-1995_12
Patent number
US05478851

Reaction notes

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