Diethyl chlorophosphate → HCID 86746781, compound

HRID 247826Notes

Reaction equation

HRID 247826 reaction equation
[O-:1][C:2]#[N:3].[K+].[P:5](Cl)([O:10][CH2:11][CH3:12])([O:7][CH2:8][CH3:9])=[O:6].[CH:14]([C:17]1[CH:23]=[CH:22][CH:21]=[C:20]([CH:24]([CH3:26])[CH3:25])[C:18]=1[NH2:19])([CH3:16])[CH3:15]>CC(C)=O>[CH3:25][CH:24]([C:20]1[CH:21]=[CH:22][CH:23]=[C:17]([CH:14]([CH3:16])[CH3:15])[C:18]=1[NH:19][C:2]([NH:3][P:5](=[O:6])([O:10][CH2:11][CH3:12])[O:7][CH2:8][CH3:9])=[O:1])[CH3:26]

Participants

5

Reactant 3

HCID 13139Diethyl chlorophosphateHCID 32484DiisopropylanilineHCID 11378442Potassium cyanate

Product 1

HCID 86746781HCID 86746781, compoundYield 39.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a suspension of potassium cyanate (0.82 g, 10.1 mmol) in acetone (10 mL) is added diethyl chlorophosphate (1.3 mL, 9.2 mmol). The mixture is heated at reflux for 90 minutes. After cooling to room temperature, 2,6-diisopropylaniline (1.7 mL, 9.2 mmol) is added. The mixture is stirred at room temperature for 2 hours, then heated at reflux for 2 hours. After cooling, the mixture is filtered. The filtrate is diluted with ethyl acetate, washed twice with brine, dried over magnesium sulfate, and concentrated. Flash chromatography (3:2 ethyl acetate/hexane) provides 1.3 g of the product as a white solid. Recrystallization from ethyl acetate/hexane provides an analytical sample; mp 157°-158° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 90 minutes
  3. temperatureheated
  4. temperatureat reflux for 2 hours
  5. temperatureAfter cooling
  6. filtrationthe mixture is filtered
  7. additionThe filtrate is diluted with ethyl acetate
  8. washwashed twice with brine
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-b64d93d3e2f44e25b4ff714f5fa836f8
Source dataset
uspto-grants-1993_05
Patent number
US05208224

Reaction notes

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