Dimethylformamide → 4-[Bis[2-(acetyloxy)ethyl]amino]benzaldehyde

HRID 359571Notes

Reaction equation

HRID 359571 reaction equation
CN(C)[CH:3]=[O:4].[C:6]([O:9][CH2:10][CH2:11][N:12]([CH2:19][CH2:20][O:21][C:22](=[O:24])[CH3:23])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:8])[CH3:7].O.O.O.C([O-])(=O)C.[Na+]>O>[C:22]([O:21][CH2:20][CH2:19][N:12]([CH2:11][CH2:10][O:9][C:6](=[O:8])[CH3:7])[C:13]1[CH:18]=[CH:17][C:16]([CH:3]=[O:4])=[CH:15][CH:14]=1)(=[O:24])[CH3:23]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 29521Ethanol, 2,2'-(phenylimino)bis-, 1,1'-diacetateHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 3287294-[Bis[2-(acetyloxy)ethyl]amino]benzaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To 450 ml of dry dimethyl formamide were slowly added dropwise with stirring and at a temperature of 0°-10° C. 100 ml of freshly distilled phosphoroxytrichloride. This mixture was stirred for 2 hours at 20° C. To this mixture there was subsequently added dropwise with proper stirring and over a period of 60 minutes the crude reaction product of the previous step, viz. N,N-di(2-acetyloxyethyl)aniline, the reaction mixture being kept at a temperature of 20° C. Next, the reaction mixture was heated to 60° C. for 60 minutes and then poured, with vigorous stirring, into a mixture of 1 kg of ice and a solution of 525 g of sodium acetate trihydrate in 1 l of water. The organic layer was separated and the water layer was extracted four times, each time with 300 ml of dichloromethane. The combined organic layers were washed three times, each time with 200 ml of water, dried on magnesium sulphate, and concentrated by evaporation. The residue (about 280 g of dark brown oil), which consisted almost entirely of 4-di(2-acetyloxyethyl)aminobenzaldehyde, was used in the next step without further purification.

Workup

  1. stirringThis mixture was stirred for 2 hours at 20° C
  2. additionTo this mixture there was subsequently added dropwise
  3. stirringwith proper stirring and over a period of 60 minutes the crude
  4. customreaction product of the previous step, viz
  5. custombeing kept at a temperature of 20° C
  6. customThe organic layer was separated
  7. extractionthe water layer was extracted four times
  8. washThe combined organic layers were washed three times
  9. dry with materialeach time with 200 ml of water, dried on magnesium sulphate
  10. concentrationconcentrated by evaporation
  11. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-2ca2f2b4414a493a89fdc5b5e73d9298
Source dataset
uspto-grants-1991_03
Patent number
US05001209

Reaction notes

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