Ethylamine → N-diethoxyphosphorylethanamine

HRID 1276802Notes

Reaction equation

HRID 1276802 reaction equation
[P:1](Cl)([O:6][CH2:7][CH3:8])([O:3][CH2:4][CH3:5])=[O:2].[CH2:10]([NH2:12])[CH3:11]>ClC(Cl)C>[CH2:10]([NH:12][P:1](=[O:2])([O:6][CH2:7][CH3:8])[O:3][CH2:4][CH3:5])[CH3:11]

Participants

4

Reactant 2

HCID 6341EthylamineHCID 13139Diethyl chlorophosphate

Product 1

HCID 264991N-diethoxyphosphorylethanamineYield 52%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 5.0 g (29.0 mmol) of diethyl chlorophosphate in 70 mL dichloroethane cooled on an ice bath was added 4.1 g (63.8 mmol) of ethylamine (70% ag). The mixture was allowed to stir at RT for 30 min and was then partitioned between ether and water. The organic layer was washed with brine, dried (MgSO4), and was filtered. The filtrate was evaporated in vacuo and the residue was kugelrohr distilled (0.8 torr, 90° C.) to yield 2.7 g (52%) of diethyl N-ethylphosphoramidate as a colorless oil.

Workup

  1. customwas then partitioned between ether and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationwas filtered
  5. customThe filtrate was evaporated in vacuo
  6. distillationdistilled (0.8 torr, 90° C.)

Sources & evidence

ORD record
ord-55f8666f752542beafbc8a955e10a7cf
Source dataset
uspto-grants-2000_12
Patent number
US06166057

Reaction notes

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