Diethyl chlorophosphate → HCID 14460515, compound

HRID 868666Notes

Reaction equation

HRID 868666 reaction equation
[CH3:1][N:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]1=O.[H-].[Na+].CCOP(Cl)(OCC)=O.[CH2:25]([C:27]1[O:31][N:30]=[C:29]([CH2:32][N+:33]#[C-:34])[N:28]=1)[CH3:26]>CN(C=O)C>[CH2:25]([C:27]1[O:31][N:30]=[C:29]([C:32]2[N:33]=[CH:34][N:4]3[C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[C:11](=[O:12])[N:2]([CH3:1])[C:3]=23)[N:28]=1)[CH3:26]

Participants

6

Reactant 4

HCID 13139Diethyl chlorophosphateHCID 24758Sodium hydrideHCID 3443853-Methyl-1,2,3,4-tetrahydroquinazoline-2,4-dioneHCID 10654277HCID 10654277, compound

Product 1

HCID 14460515HCID 14460515, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-methyl-1,2,3,4-tetrahydro-2,4-dioxo-quinazoline (5 mmol) was dissolved in dry dimethyl formamide DMF (20 ml) and charged with sodium hydride (6 mmol). The resulting solution was cooled under N2 to -20° C., whereafter chlorodiethylphosphate (6 mmol) was added. The reaction mixture was kept under N2 with stirring and was allowed to reach room temperature and was then charged with a -30° C. cold solution of 5-ethyl-3-isocyanomethyl-1,2,4-oxadiazole (6 mmol) and K-t-butylate (6 mmol) in dry DMF (15 ml). The resulting mixture was stirred at room temperature for one hour whereafter the reaction mixture was evaporated in vacuo. The residue was partitioned between ethyl acetate and 4M sodium hydroxide. The organic phase was dried and evaporated. Yield 120 mg of title compound. M.p. 199.4°-202.2° C.

Workup

  1. additionwas added
  2. customto reach room temperature
  3. stirringThe resulting mixture was stirred at room temperature for one hour whereafter the reaction mixture
  4. customwas evaporated in vacuo
  5. customThe residue was partitioned between ethyl acetate and 4M sodium hydroxide
  6. customThe organic phase was dried
  7. customevaporated

Sources & evidence

ORD record
ord-124826622dc74dc1ae27298e123e87cc
Source dataset
uspto-grants-1988_10
Patent number
US04780539

Reaction notes

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