Benzaldehyde → [(benzylamino)-phenylmethyl]phosphonic acid

HRID 325757Notes

Reaction equation

HRID 325757 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:9]([NH2:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[P:17]([OH:20])([OH:19])[OH:18]>C(=O)([O-])[O-].[Na+].[Na+]>[CH2:1]([NH:16][CH:9]([P:17](=[O:18])([OH:20])[OH:19])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 7504BenzylamineHCID 107909Phosphorous acid

Product 1

HCID 4469578[(benzylamino)-phenylmethyl]phosphonic acid

Reagents, catalysts & solvents 1

HCID 10340Sodium CarbonateSolvent

Procedure

The imine from benzaldehyde and benzylamine (65 g; 0.33 mole) was added to phosphorous acid (27.3 g; 0.33 mole) and the mixture stirred with heating. As the temperature reached 95°-100° the whole mixture became a homogeneous liquid which reacted vigorously as the temperature reached 115°-120°. The reaction mass became very viscous and was allowed to cool to a glass. This glass was dissolved in aqueous sodium carbonate and upon acidification gave N-benzyl α-aminobenzylphosphonic acid, mp 233°-4°, 90 g (98%).

Workup

  1. temperaturewith heating
  2. customreached 95°-100°
  3. customreacted vigorously as the temperature
  4. customreached 115°-120°
  5. temperatureto cool to a glass

Sources & evidence

ORD record
ord-0649751143724c3abfc0105473a5e3f7
Source dataset
uspto-grants-1984_04
Patent number
US04442286

Reaction notes

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