Diethanolamine → HCID 520063, compound

HRID 1939873Notes

Reaction equation

HRID 1939873 reaction equation
[NH:1]([CH2:5][CH2:6][OH:7])[CH2:2][CH2:3][OH:4].C(N(CC)CC)C.[CH2:15]([O:17][P:18](Cl)([O:20][CH2:21][CH3:22])=[O:19])[CH3:16]>ClCCl.CCOCC>[CH2:15]([O:17][P:18]([N:1]([CH2:5][CH2:6][OH:7])[CH2:2][CH2:3][OH:4])([O:20][CH2:21][CH3:22])=[O:19])[CH3:16]

Participants

6

Reactant 3

HCID 8113DiethanolamineHCID 8471TriethylamineHCID 13139Diethyl chlorophosphate

Product 1

HCID 520063HCID 520063, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of diethanolamine (5.0 g, 48 mmol) and triethylamine (8.0 ml) in dichloromethane (75 ml) was added dropwise with stirring under Argon, a solution of diethylchlorophosphate (8.2 g, 48 mmol) in dichloromethane (25 ml) over approximately 15 minutes and then allowed to stir at room temperature overnight. The mixture was washed with brine (50 ml) then dried (Na2SO4) and evaporated in vacuo to give the crude product as a viscous oil. The oil was dissolved in ether (100 ml) and the white solid which precipitated was filtered off (triethylamine hydrochloride). The ether solution was evaporated in vacuo giving N-diethoxyphosphoryldiethanolamine (6.2 g, 54%) as a colourless oil.

Workup

  1. stirringto stir at room temperature overnight
  2. washThe mixture was washed with brine (50 ml)
  3. dry with materialthen dried (Na2SO4)
  4. customevaporated in vacuo
  5. customto give the crude product as a viscous oil
  6. customthe white solid which precipitated
  7. filtrationwas filtered off (triethylamine hydrochloride)
  8. customThe ether solution was evaporated in vacuo

Sources & evidence

ORD record
ord-1a36ba33b9eb4244ab070ff96dcd287c
Source dataset
uspto-grants-1997_12
Patent number
US05698546

Reaction notes

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