Water → Benzaldehyde, 4-[[2-(acetyloxy)ethyl]ethylamino]-

HRID 983574Notes

Reaction equation

HRID 983574 reaction equation
[CH2:1]([N:3]([CH2:10][CH2:11][O:12][C:13](=[O:15])[CH3:14])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2].O.CN([CH:20]=[O:21])C>>[CH2:1]([N:3]([CH2:10][CH2:11][O:12][C:13](=[O:15])[CH3:14])[C:4]1[CH:9]=[CH:8][C:7]([CH:20]=[O:21])=[CH:6][CH:5]=1)[CH3:2]

Participants

4

Reactant 3

HCID 962WaterHCID 6228Dimethylformamide2×HCID 113382Ethanol, 2-(ethylphenylamino)-, 1-acetate

Product 1

HCID 11458991Benzaldehyde, 4-[[2-(acetyloxy)ethyl]ethylamino]-

Conditions

Temperature
5 °C

Procedure

To 60 ml of dry DMF in a 250 ml-flask, equipped with a CaCl2-tube, cooled in an ice bath, 29.1 (310 mmol) of OPCl3 is dropwise added and the mixture is stirred for two h at 5° C. Then, 58.5 g (288 mmol) of 16, dissolved in 30 ml of dry DMF, is added and the reaction mixture is stirred for 3 h at 90° C. After cooling down, the mixture is poured into iced water, stirred for 30 min and extracted with dichloromethane. The organic layer is washed with a saturated NaHCO3-solution, with brine and dried over MgSO4. After evaporation of the solvent, the compound is purified with column chromatography (silicagel; eluent:dichloromethane/acetonitrile (90:10 v/v)) and collected as an oil.

Workup

  1. temperaturecooled in an ice bath
  2. additionis added
  3. stirringthe reaction mixture is stirred for 3 h at 90° C
  4. temperatureAfter cooling down
  5. stirringstirred for 30 min
  6. extractionextracted with dichloromethane
  7. washThe organic layer is washed with a saturated NaHCO3-solution, with brine
  8. dry with materialdried over MgSO4
  9. customAfter evaporation of the solvent
  10. customthe compound is purified with column chromatography (silicagel; eluent:dichloromethane/acetonitrile (90:10 v/v))
  11. customcollected as an oil

Sources & evidence

ORD record
ord-938c63d2d8d9493dbf7f6a07dfaf0d19
Source dataset
uspto-grants-2005_03
Patent number
US06864347B2

Reaction notes

Loading…