Triethylamine → P,P-Diphenyl-N-(phenylmethylene)phosphinic amide

HRID 266664

Reaction equation

HRID 266664 reaction equation
[CH:1](=[N:8]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:17]1([P:23](Cl)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(Cl)Cl>[C:17]1([P:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)(=[O:24])[N:8]=[CH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12143(Z)-Benzaldehyde oximeHCID 73910Diphenylphosphinic chloride

Product 1

HCID 608413P,P-Diphenyl-N-(phenylmethylene)phosphinic amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-50 °C

Procedure

A dry 250 mL 3-necked round bottom flask, fitted with a magnetic stir bar, addition funnel and thermometer, was charged with benzaldehyde oxime (38 mmol) dissolved in petroleum ether (40 mL) and methylene chloride (40 mL) along with triethylamine (38 mmol). The flask was cooled, under an atmosphere of nitrogen, to -50° C. with a Dry Ice-chloroform bath. The addition funnel was charged with diphenylphosphinyl chloride (37 mmol) dissolved in methylene chloride (10 mL) and this solution was slowly dropped into the flask ensuring that the reaction temperature did not rise above -25° C. White precipitate formation was observed. Once the addition was complete the reaction temperature was naturally allowed to rise to room temperature over a period of 2 hours. The reaction mixture was filtered to remove the precipitate and the filtrate was concentrated by rotary evaporation which yielded a yellow oil which solidified upon standing. The structure of the product is detailed below. ##STR8##

Workup

  1. customA dry 250 mL 3-necked round bottom flask, fitted with a magnetic stir bar, addition funnel
  2. additionthis solution was slowly dropped into the flask
  3. customdid not rise above -25° C
  4. additionOnce the addition
  5. filtrationThe reaction mixture was filtered
  6. customto remove the precipitate
  7. concentrationthe filtrate was concentrated by rotary evaporation which
  8. customyielded a yellow oil which

Sources & evidence

ORD record
ord-bb18bc54e42742c8bd08f38804c42486
Source dataset
uspto-grants-1997_07
Patent number
US05652207

Linked notes

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