Ethylamine → N-diethoxyphosphorylethanamine

HRID 356434Notes

Reaction equation

HRID 356434 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% aq). 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-fc4cbe5333bb483e8b904ff1a773e58a
Source dataset
uspto-grants-1998_11
Patent number
US05834447

Reaction notes

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