Acetic Anhydride → Diethyl[3-(acetylamino)propyl]phosphonate

HRID 2071856

Reaction equation

HRID 2071856 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][CH2:10][CH2:11][NH2:12])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].[C:13](OC(=O)C)(=[O:15])[CH3:14]>N1C=CC=CC=1>[CH2:6]([O:5][P:4]([CH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:15])[CH3:14])(=[O:8])[O:3][CH2:1][CH3:2])[CH3:7]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 78113Diethyl (3-aminopropyl)phosphonate

Product 1

HCID 254237Diethyl[3-(acetylamino)propyl]phosphonateYield 96%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

97 g. of 3-aminopropanephosphonic acid diethyl ester is dissolved in 400 ml. of dry pyridine and 55 g. of acetic anhydride is added with stirring. The mixture is then boiled for 4 hours with refluxing and freed of the low-boiling components by evaporation in a light vacuum. Gaschromatographically pure N-acetyl-3-aminopropanephosphonic acid diethyl ester is obtained in a 96% yield by shortcut distillation in vacuo. It is a pale yellow, highly viscous oil with a boiling point of 166° to 160° C (0.4 Torr).

Workup

  1. temperaturewith refluxing
  2. customfreed of the low-boiling components by evaporation in a light vacuum

Sources & evidence

ORD record
ord-5ba0b0e248f047ae9164df73aefc584c
Source dataset
uspto-grants-1977_09
Patent number
US04048374

Linked notes

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