Sodium Sulfite → 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 35819Notes

Reaction equation

HRID 35819 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.S([O-])([O-])=O.[Na+].[Na+]>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

5

Reactant 3

HCID 24437Sodium SulfiteHCID 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 6212ChloroformSolvent2×

Procedure

In 500 ml of chloroform, 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, to which 30.0 g of m-chloroperbenzoic acid was added, and the reaction was effected at 60° C. for 4.5 :hours. After completion of the reaction, the reaction mixture was cooled to room temperature and subjected to fractionation with a separatory funnel using chloroform and an aqueous solution of sodium sulfite. The organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate and then water, dried and concentrated. The residue was subjected to recrystallization, which afforded 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. customwas effected at 60° C. for 4.5
  3. customAfter completion of the reaction
  4. customsubjected to fractionation with a separatory funnel
  5. washThe organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate
  6. dry with materialwater, dried
  7. concentrationconcentrated
  8. customThe residue was subjected to recrystallization, which

Sources & evidence

ORD record
ord-619f77666ca94733b69a104a734e343f
Source dataset
uspto-grants-1995_05
Patent number
US05411935

Reaction notes

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