Formaldehyde → Dibenzyl P-(N-tert-Butyl-N-hydroxyaminomethyl)phosphonate

HRID 846838

Reaction equation

HRID 846838 reaction equation
Cl.[C:2]([NH:6][OH:7])([CH3:5])([CH3:4])[CH3:3].C=O.[P:10]([O-:27])([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[C:28](=O)(O)[O-].[Na+]>O1CCCC1>[C:2]([N:6]([CH2:28][P:10](=[O:27])([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[OH:7])([CH3:5])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 2777896N-tert-butylhydroxylamine hydrochlorideHCID 21904359Dibenzylphosphite

Product 1

HCID 19883778Dibenzyl P-(N-tert-Butyl-N-hydroxyaminomethyl)phosphonateYield 64%

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 (40 mmol) of N-tert-butylhydroxylamine hydrochloride, 2.4 g (80 mmol) of paraformaldehyde, 9.0 g (41 mmol) of dibenzyl phosphite, 3.0 g (40 mmol) of sodium bicarbonate and 200 ml of tetrahydrofuran (THF) by heating at 55° C. for 14 hours. The residue is purified by recrystallization from a mixture of methylene chloride and hexane to give 9.2 g (64% yield) of a white solid melting at 106°-107° C.

Workup

  1. customThe residue is purified by recrystallization from a mixture of methylene chloride and hexane

Sources & evidence

ORD record
ord-8b4937138b114f51953c304be4aae8cb
Source dataset
uspto-grants-1992_08
Patent number
US05137951

Linked notes

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