Ammonia → Diethyl (aminomethyl)phosphonate

HRID 1657991Notes

Reaction equation

HRID 1657991 reaction equation
Cl.[NH2:2][CH2:3][P:4](=[O:11])([O:8][CH2:9][CH3:10])[O:5][CH2:6][CH3:7].N>C(Cl)(Cl)Cl>[NH2:2][CH2:3][P:4](=[O:11])([O:8][CH2:9][CH3:10])[O:5][CH2:6][CH3:7]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 12753802HCID 12753802, compound

Product 1

HCID 1596920Diethyl (aminomethyl)phosphonateYield 98.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Diethyl aminomethylphosphonate hydrochloride (4.965 g.) is stirred in chloroform (25 ml.) at 0°C. while ammonia is bubbled through the mixture for 4 minutes. The resulting ammonium chloride is filtered off and the filtrate dried briefly over MgSO4. Evaporation of the solvent at reduced pressure affords diethyl aminomethylphosphonate (4.031 g.) as a clear liquid. ir (CCl4) 1240, 1062, 1032, and 966 cm-1 ; nmr (CDCl3)τ8.67 (t, 6, J=7Hz, CH3), 7.03 (d, 2, J=11Hz, CH2), and 5.86 (p, 4, J=7Hz and J=7Hz, CH2CH3).

Workup

  1. customis bubbled through the mixture for 4 minutes
  2. filtrationThe resulting ammonium chloride is filtered off
  3. dry with materialthe filtrate dried briefly over MgSO4
  4. customEvaporation of the solvent at reduced pressure

Sources & evidence

ORD record
ord-bb61fd4f2b76461185471c0c65bb2e3a
Source dataset
uspto-grants-1976_06
Patent number
US03962224

Reaction notes

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