Phosphorus oxychloride → 6-Chloro-3-(propan-2-yl)-1,2,3,4-tetrahydropyrimidine-2,4-dione

HRID 1380401Notes

Reaction equation

HRID 1380401 reaction equation
P(Cl)(Cl)([Cl:3])=O.[CH:6]([N:9]1[C:16](=[O:17])[CH2:15][C:13](=O)[NH:12][C:10]1=[O:11])([CH3:8])[CH3:7]>O>[CH:6]([N:9]1[C:16](=[O:17])[CH:15]=[C:13]([Cl:3])[NH:12][C:10]1=[O:11])([CH3:8])[CH3:7]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 2319626-Hydroxy-3-(propan-2-yl)pyrimidine-2,4(3H,5H)-dione

Product 1

HCID 8201076-Chloro-3-(propan-2-yl)-1,2,3,4-tetrahydropyrimidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

350 ml of phosphorus oxychloride containing 15 ml of water are slowly run into 75 g (0.44 mole) of 1-isopropyl barbituric acid. After the violent exothermic reaction has abated, the reaction mixture is refluxed for 1 hour. The excess POCl3 is removed by evaporation in vacuo and the oily residue is poured onto ice, giving a precipitate which is filtered, washed with ice water and dried. 55 g of yellowish crystals are thus obtained.

Workup

  1. customAfter the violent exothermic reaction
  2. temperaturethe reaction mixture is refluxed for 1 hour
  3. customThe excess POCl3 is removed by evaporation in vacuo
  4. additionthe oily residue is poured onto ice
  5. customgiving a precipitate which
  6. filtrationis filtered
  7. washwashed with ice water
  8. customdried

Sources & evidence

ORD record
ord-fed5984469034dd99e77f3de53f258de
Source dataset
uspto-grants-1986_04
Patent number
US04581451

Reaction notes

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