Diethyl chlorophosphate → HCID 19817942, compound

HRID 1087271Notes

Reaction equation

HRID 1087271 reaction equation
[CH3:1][C:2]1[C:3](O)=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[H-].[Na+].CCOP(Cl)(OCC)=O.[N+:24]([CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])#[C-:25].CC(C)([O-])C.[K+]>CN(C=O)C.C(O)(=O)C>[CH3:1][C:2]1[C:3]2[N:4]([CH:25]=[N:24][C:26]=2[C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

8

Reactant 5

HCID 13139Diethyl chlorophosphateHCID 24758Sodium hydrideHCID 533707Ethyl isocyanoacetateHCID 23665647Potassium tert-butoxideHCID 178418588HCID 178418588, compound

Product 1

HCID 19817942HCID 19817942, compoundYield 54.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent2×

Procedure

3-Methyl-2-quinoxalinol (2.84 g, 18 mmol) was dissolved in dry DMF (40 ml) and charged with sodium hydride (55% oil dispersion, 1.0 g, 23 mmol). The resulting solution was cooled under nitrogen to -20° C., whereafter chlorodiethylphosphate (3.3 ml, 23 mmol) was added. The reaction mixture was allowed to reach room temperature, and was then added a -30° C. cold solution of ethyl isocyanoacetate (2.6 g, 23 mmol) and potassium t-butoxide (2.6 g, 23 mmol) in dry DMF (25 ml). The mixture was stirred for 45 min. at ambient temperature, whereafter acetic acid (3 ml) was added. The crystalline precipitate was collected by filtration, rinsed with DMF and water and dried, yielding 2.5 g of the title compound. M.p. 192°-193° C. (Compound 1)

Workup

  1. additionwas added
  2. customto reach room temperature
  3. additionwas added
  4. filtrationThe crystalline precipitate was collected by filtration
  5. washrinsed with DMF and water
  6. customdried

Sources & evidence

ORD record
ord-75239a4456ea4ec6856b30b9c97b1992
Source dataset
uspto-grants-1991_07
Patent number
US05034530

Reaction notes

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