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

HRID 1941483Notes

Reaction equation

HRID 1941483 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]1([P:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:17])[NH2:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(N(CC)CC)C>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[C:9]1([P:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:17])[N:16]=[CH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 8471TriethylamineHCID 853560Diphenylphosphinamide

Product 1

HCID 608413P,P-Diphenyl-N-(phenylmethylene)phosphinic amideYield 40%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

P,P-diphenyl-N-phenylmethylene phosphinic amide was prepared following the method of Jennings (ibid) by adding titanium tetrachloride (635 ml; 5.78 mmol) in dry dichloromethane (10 ml) to a stirred solution of benzaldehyde (1.17 ml; 11.59 mmol), P,P-diphenylphosphinic amide (2.52 g; 11.59 mmol) and anhydrous triethylamine (4.84 ml; 34.78 mmol) in dry dichloromethane (50 ml) at 0° C. Upon completion of the addition, the stirring was maintained at 0° C. for a further 4 hours. Subsequent work-up gave P,P-diphenyl-N-phenylmethylene phosphinic amide (1.4 g; 40%).

Workup

  1. customP,P-diphenyl-N-phenylmethylene phosphinic amide was prepared
  2. additionUpon completion of the addition

Sources & evidence

ORD record
ord-b61ac70fc6c24d4ebf0ab98b7bfc3d55
Source dataset
uspto-grants-1997_12
Patent number
US05703246

Reaction notes

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