Benzamide → HCID 438132, compound

HRID 1576057Notes

Reaction equation

HRID 1576057 reaction equation
[C:1]([NH2:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Br)(Br)Br.[P:14]([OH:17])([OH:16])[OH:15]>O1CCOCC1.O>[C:2]1([C:1]([NH2:9])([P:14]([OH:17])(=[O:15])[OH:16])[P:14]([OH:17])(=[O:16])[OH:15])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 2331BenzamideHCID 24614Phosphorus tribromideHCID 107909Phosphorous acid

Product 1

HCID 438132HCID 438132, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

120 parts of benzamide were suspended in 300 parts of dioxan and reacted with 541 parts of phosphorus tribromide. Then 82 parts of phosphorous acid dissolved in dioxan were added at about 20°C, and the mixture was heated at 60° to 70° C for 3 to 4 hours. The reaction mixture was poured on ice and then concentrated. Subsequently, the mixture was extracted with acetone and then with ether. The residue was isolated, dissolved in water and precipitated again with ethyl acetate/acetone. The precipitate, the trihydrate of 1-phenyl-1-aminomethane-1,1-diphosphonic acid was isolated and dried in air. The yield amounts to 18%, based on PBr3.

Workup

  1. additionwere added at about 20°C
  2. temperaturethe mixture was heated at 60° to 70° C for 3 to 4 hours
  3. additionThe reaction mixture was poured on ice
  4. concentrationconcentrated
  5. extractionSubsequently, the mixture was extracted with acetone
  6. customThe residue was isolated
  7. customprecipitated again with ethyl acetate/acetone

Sources & evidence

ORD record
ord-2b49f04cf3164772b6fd99dfed75acb5
Source dataset
uspto-grants-1976_09
Patent number
US03979385

Reaction notes

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