Acetone → 1-Benzhydrylamino-2-methylpropanephosphonous acid

HRID 1677606Notes

Reaction equation

HRID 1677606 reaction equation
[C:1]1([CH:7]([NH2:14])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[PH2:15]([OH:17])=[O:16].[C:18](=O)([CH3:20])[CH3:19].[CH2:22](O)C>CCOCC>[C:1]1([CH:7]([NH:14][CH:19]([P:15]([OH:17])[OH:16])[CH:18]([CH3:20])[CH3:22])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 702Ethanol2×HCID 7036BenzhydrylamineHCID 4124402Phosphinic Acid

Product 1

HCID 213258821-Benzhydrylamino-2-methylpropanephosphonous acid

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Diphenylmethylamine (34 mL, 0.2 mol) was added dropwise to a solution of 100% hypophosphorous acid (13.2 g, 0.2 mol) in 100 mL of absolute ethanol. The resulting mixture was stirred at ambient temperature for 15 minutes, then diluted with 500 mL of ether. The precipitated salt (45 g) was collected by filtration. The salt (25 g, 0.1 mol) was dissolved in 50 mL of absolute ethanol and the isopropanal (9 mL, 0.1 mol) (a compound of formula (Xb)) was added. The reaction mixture was heated at reflux for 3 hours. On cooling, the product formed as a precipitate. The product was removed by filtration and washed with ethanol and ether to afford 1-(diphenylmethylamino)-2-methylpropylphosphonous acid (a compound of formula (Xc)) as a white solid (12.5 g) that was used in the next step without further purification.

Workup

  1. filtrationThe precipitated salt (45 g) was collected by filtration
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux for 3 hours
  4. temperatureOn cooling
  5. customthe product formed as a precipitate
  6. customThe product was removed by filtration
  7. washwashed with ethanol and ether

Sources & evidence

ORD record
ord-815c40f264aa476ab0f91f4ae86c9093
Source dataset
uspto-grants-2011_08
Patent number
US08008325B2

Reaction notes

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