Formaldehyde → Dimethyl {[benzyl(hydroxy)amino]methyl}phosphonate

HRID 846839Notes

Reaction equation

HRID 846839 reaction equation
Cl.[CH2:2]([NH:9][OH:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C=O.[P:13]([O-:18])([O:16][CH3:17])[O:14][CH3:15].[C:19](=O)(O)[O-].[Na+]>C1COCC1>[CH2:2]([N:9]([CH2:19][P:13](=[O:18])([O:16][CH3:17])[O:14][CH3:15])[OH:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 11332622N-benzylhydroxylamine hydrochlorideHCID 21884954Dimethylphosphite

Product 1

HCID 19883777Dimethyl {[benzyl(hydroxy)amino]methyl}phosphonateYield 82.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

Using the procedure of Example 1, the above-named compound is prepared from 5.0 g (31 mmol) of N-benzylhydroxylamine hydrochloride, 1.8 g (60 mmol) of paraformaldehyde, 3.7 ml (40 mmol) of dimethyl phosphite, 2.5 g (30 mmol) of sodium bicarbonate and 350 ml of THF by heating at 55° C. for seven hours. The residue is purified by column chromatography (silica gel, methylene chloride:ethyl acetate eluent) to give 6.1 g (80% yield) of a viscous colorless liquid.

Workup

  1. customThe residue is purified by column chromatography (silica gel, methylene chloride:ethyl acetate eluent)

Sources & evidence

ORD record
ord-58a0f5dc1e4b461aba81a29048117cb5
Source dataset
uspto-grants-1992_08
Patent number
US05137951

Reaction notes

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