Phosphorus oxychloride → HCID 58076128, compound

HRID 78686Notes

Reaction equation

HRID 78686 reaction equation
[N+:1]([C:3]1[CH:19]=[CH:18][CH:17]=[CH:16][C:4]=1[CH2:5][N:6]1[C:11](=O)[CH2:10][C:9](=[O:13])[N:8]([CH3:14])[C:7]1=[O:15])#[C-:2].P(Cl)(Cl)([Cl:22])=O.P(Cl)(Cl)(Cl)(Cl)Cl>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(#N)C>[Cl:22][C:11]1[N:6]([CH2:5][C:4]2[CH:16]=[CH:17][CH:18]=[CH:19][C:3]=2[N+:1]#[C-:2])[C:7](=[O:15])[N:8]([CH3:14])[C:9](=[O:13])[CH:10]=1

Participants

6

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachlorideHCID 580761231-(2-isocyanobenzyl)-3-methylpyrimidine-2,4,6(1H,3H,5H)-trione

Product 1

HCID 58076128HCID 58076128, compoundYield 70.5%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

In an alternate embodiment, a solution of 1-(2-isocyanobenzyl)-3-methylpyrimidine-2,4,6(1H,3H,5H)-trione (18 mmol), phosphorus oxychloride (85 ml), benzyltriethylammonium chloride (16.5 g, 72 mmol) and phosphorus pentachloride (3.8 g, 18 mol) in acetonitrile (80 ml) was refluxed for 4-5 h with stirring. After evaporation under reduced pressure, the resulting oily residue was mixed with methylene chloride (or chloroform) and the mixture was poured into water and ice (50 ml). The layers were separated and the aqueous layer was extracted with dichloromethane (200 ml). The combined organic extracts were washed with water and brine, dried over sodium sulphate and concentrated under reduced pressure. Crude product was crystallized from THF-hexanes to give desired compound in 70.5% yield.

Workup

  1. customAfter evaporation under reduced pressure
  2. additionthe resulting oily residue was mixed with methylene chloride (or chloroform)
  3. additionthe mixture was poured into water and ice (50 ml)
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with dichloromethane (200 ml)
  6. washThe combined organic extracts were washed with water and brine
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated under reduced pressure
  9. customCrude product was crystallized from THF-hexanes

Sources & evidence

ORD record
ord-b8c62efd42a040d2bb3699569c50f00e
Source dataset
uspto-grants-2014_09
Patent number
US08841447B2

Reaction notes

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