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

HRID 359571노트

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HRID 359571 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

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온도
60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2ca2f2b4414a493a89fdc5b5e73d9298
출처 데이터셋
uspto-grants-1991_03
특허 번호
US05001209

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