Acetic Anhydride → Sodium

HRID 839253Notes

Reaction equation

HRID 839253 reaction equation
[Na:1].[NH2:2][C:3]([P:9]([OH:12])(=[O:11])[OH:10])([P:5]([OH:8])(=[O:7])[OH:6])[CH3:4].[C:13](OC(=O)C)(=[O:15])[CH3:14]>O>[Na:1].[C:13]([NH:2][C:3]([P:5]([OH:8])(=[O:6])[OH:7])([P:9]([OH:12])(=[O:10])[OH:11])[CH3:4])(=[O:15])[CH3:14]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 84770(1-Aminoethylidene)bisphosphonic acidHCID 5360545Sodium

Product 2

HCID 5360545SodiumHCID 22155105Phosphonic acid, [1-(acetylamino)ethylidene]bis-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

22.7 g. (0.1 mole) of the mono-sodium salt of 1-amino ethane-1,1-diphosphonic acid are boiled under reflux in 30.6 g. (0.3 moles) of acetic acid anhydride for about 30 minutes. A clear solution is obtained. On cooling, a viscous yellowish sirup is produced. The sirup can be diluted with water and the aqueous solution can be used directly. In order to recover the crystalline reaction product, the sirup is added with stirring to 40 cc. of glacial acetic acid and the resulting crystalline product is filtered off by suction. After drying, 20.3 g. of the mono-sodium salt of N-acetyl-1-amino ethane-1,1-diphosphonic acid, corresponding to 75.4 % of the theoretical yield, are obtained.

Workup

  1. temperatureunder reflux in 30.6 g
  2. customA clear solution is obtained
  3. temperatureOn cooling
  4. customa viscous yellowish sirup is produced
  5. customIn order to recover the crystalline reaction product
  6. additionthe sirup is added
  7. filtrationof glacial acetic acid and the resulting crystalline product is filtered off by suction
  8. customAfter drying

Sources & evidence

ORD record
ord-cf4cad4070bb4356b0b07f7fec9a63d8
Source dataset
uspto-grants-1978_06
Patent number
US04094782

Reaction notes

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