m-Chloroperbenzoic acid → 1-[4-Chloro-6-fluoro-3-hydroxy-2-(2,3-epoxy-2-methylpropyl)phenyl]-3-methyl-4-trifluoromethyl-1,2,3,6-tetrahydropyrimidine-2,6-dione

HRID 861297Notes

Reaction equation

HRID 861297 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N:9]2[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[N:11]([CH3:20])[C:10]2=[O:21])=[C:4]([CH2:22][C:23]([CH3:25])=[CH2:24])[C:3]=1[OH:26].ClC1C=CC=C(C(OO)=[O:35])C=1>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N:9]2[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:18])([F:19])[F:17])[N:11]([CH3:20])[C:10]2=[O:21])=[C:4]([CH2:22][C:23]2([CH3:25])[O:35][CH2:24]2)[C:3]=1[OH:26]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 152799451-[4-Chloro-6-fluoro-3-hydroxy-2-(2-methyl-2-propenyl)phenyl]-3-methyl-4-trifluoromethyl-1,2,3,6-tetrahydropyrimidine-2,6-dione

Product 1

HCID 197027661-[4-Chloro-6-fluoro-3-hydroxy-2-(2,3-epoxy-2-methylpropyl)phenyl]-3-methyl-4-trifluoromethyl-1,2,3,6-tetrahydropyrimidine-2,6-dioneYield 88.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

First, 50 g of 1-[4-chloro-6-fluoro-3-hydroxy-2-(2-methyl-2-propenyl)phenyl]-3-methyl-4-trifluoromethyl-1,2,3,6-tetrahydropyrimidine-2,6-dione was dissolved in 500 ml of chloroform, to which 30.0 g of m-chloroperbenzoic acid was added, and the reaction was allowed to proceed at 60° C. for 4.5 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and subjected to phase separation with chloroform and aqueous sodium sulfite solution. The organic layer was successively washed with saturated aqueous sodium bicarbonate solution and water, dried and concentrated. The residue was recrystallized to afford 46 g of 1-[4-chloro-6-fluoro-3-hydroxy-2-(2,3-epoxy-2-methylpropyl)phenyl]-3-methyl-4-trifluoromethyl-1,2,3,6-tetrahydropyrimidine-2,6-dione.

Workup

  1. additionwas added
  2. customAfter completion of the reaction
  3. customsubjected to phase separation with chloroform and aqueous sodium sulfite solution
  4. washThe organic layer was successively washed with saturated aqueous sodium bicarbonate solution and water
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was recrystallized

Sources & evidence

ORD record
ord-773deac7f58d4b1185217be31a118a9a
Source dataset
uspto-grants-1998_02
Patent number
US05714437

Reaction notes

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