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

HRID 2291431Notes

Reaction equation

HRID 2291431 reaction equation
[C:1]([O:4][CH2:5][CH2:6][N:7]([CH2:14][CH2:15][O:16][C:17](=[O:19])[CH3:18])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=[O:3])[CH3:2].P(Cl)(Cl)(Cl)=O.CN([CH:28]=[O:29])C>>[C:17]([O:16][CH2:15][CH2:14][N:7]([CH2:6][CH2:5][O:4][C:1](=[O:3])[CH3:2])[C:8]1[CH:13]=[CH:12][C:11]([CH:28]=[O:29])=[CH:10][CH:9]=1)(=[O:19])[CH3:18]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 29521Ethanol, 2,2'-(phenylimino)bis-, 1,1'-diacetate

Product 1

HCID 3287294-[Bis[2-(acetyloxy)ethyl]amino]benzaldehydeYield 93%

Procedure

N,N-Di-(2-acetoxyethyl)aniline (A6) (126 g, 0.476 mol) was reacted with phosphorous oxychloride (80.3 g, 0.524 mol) in DMF as for A2 in Example 3. The product was distilled at 155°-175° C. (0.15 mm) to yield 130 g (93%) of A7 as an orange oil.

Workup

  1. distillationThe product was distilled at 155°-175° C. (0.15 mm)

Sources & evidence

ORD record
ord-05a49bd50ddd4a34b18906cf3394db88
Source dataset
uspto-grants-1989_01
Patent number
US04796971

Reaction notes

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