Acetic Anhydride → Sodium

HRID 437095Notes

Reaction equation

HRID 437095 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-43e8e1ab3e064ea3a83b2411ef5b8b23
Source dataset
uspto-grants-1977_06
Patent number
US04029697

Reaction notes

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