Phosphorus oxychloride → 6-Chloro-3-methyl-1-phenylpyrimidine-2,4(1H,3H)-dione

HRID 2258474Notes

Reaction equation

HRID 2258474 reaction equation
O[C:2]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:6](=[O:14])[N:5]([CH3:15])[C:4](=[O:16])[CH:3]=1.P(Cl)(Cl)([Cl:19])=O>O>[Cl:19][C:2]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:6](=[O:14])[N:5]([CH3:15])[C:4](=[O:16])[CH:3]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178481542HCID 178481542, compound

Product 1

HCID 150462236-Chloro-3-methyl-1-phenylpyrimidine-2,4(1H,3H)-dioneYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

To the obtained 6-hydroxy-3-methyl-1-phenyluracil (12.2 g, 56 mM) was added phosphorus oxychloride (phosphoryl chloride, 167 ml, 2M) under cooling with ice and 3.4 ml of water was then added dropwise. The solution was heated gradually and maintained at 110° C. for 2 hours. The solvent was distilled off under reduced pressure. A product was obtained by crystallization with water and recovered by filtration to yield 6-chloro-3-methyl-1-phenyluracil (yield: 9.55 g, or 72% based on 6-hydroxy-3-methyl-1-phenyluracil).

Workup

  1. additionwas then added dropwise
  2. temperatureThe solution was heated gradually
  3. distillationThe solvent was distilled off under reduced pressure
  4. customA product was obtained by crystallization with water
  5. filtrationrecovered by filtration

Sources & evidence

ORD record
ord-aef82a322e694f9892b773aefa64cf7c
Source dataset
uspto-grants-1997_08
Patent number
US05661153

Reaction notes

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