Water → Benzoylaminomethanephosphonic acid
Reaction equation
C(OC(=O)C)(=O)C.[P:8]([OH:11])([OH:10])[OH:9].O[CH2:13][NH:14][C:15](=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O>C(O)(=O)C>[C:15]([NH:14][CH2:13][P:8]([OH:11])(=[O:10])[OH:9])(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
561 g (5.5 mol) of acetic anhydride were cooled to 10° C. Then, a solution of 164 g (2.0 mol) of phosphorous acid and 300 ml of acetic acid were added dropwise in the course of one hour, with stirring and cooling. 302 g (2.0 mol) of N-hydroxymethylbenzamide were then added in portions in the course of 50 minutes at 10°-15° C., with cooling. Stirring was continued at 10° C. for 20 minutes. The reaction mixture was subsequently kept under reflux for 2.5 hours, followed by cooling. 61 g (3.39 mol) of water were then added dropwise at 25°-30° C., with cooling and stirring. After this, the mixture was refluxed again. After cooling, the mixture was stirred overnight and solids were then filtered off with suction. 320 g (approx. 75% of theory) of crude benzoylaminomethanephosphonic acid were obtained. Further crude acid could be obtained from the mother liquor.
Workup
- temperaturecooling
- temperaturewith cooling
- stirringStirring
- temperatureunder reflux for 2.5 hours
- temperatureby cooling
- temperaturewith cooling
- stirringstirring
- temperatureAfter this, the mixture was refluxed again
- temperatureAfter cooling
- stirringthe mixture was stirred overnight
- filtrationsolids were then filtered off with suction
Sources & evidence
- ORD record
- ord-80c8920d283c4f959e85cb14abc98b2b
- Source dataset
- uspto-grants-1995_07
- Patent number
- US05432291
Reaction notes
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