Sodium Hydroxide → 5-(5-Phenyl-2-furyl)oxazolidine-2,4-dione

HRID 1262930Notes

Reaction equation

HRID 1262930 reaction equation
[OH:1][C:2]1([C:11]2[O:12][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:14][CH:15]=2)C(=O)N[C:5](=[O:9])[NH:4][C:3]1=[O:10].[OH-].[Na+]>>[C:16]1([C:13]2[O:12][C:11]([CH:2]3[O:1][C:5](=[O:9])[NH:4][C:3]3=[O:10])=[CH:15][CH:14]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 129626675-hydroxy-5-(5-phenyl-2-furyl)-2,4,6(1H,3H,5H)-pyrimidinetrione

Product 1

HCID 129626685-(5-Phenyl-2-furyl)oxazolidine-2,4-dioneYield 16.8%

Procedure

5-Hydroxy-5-(5-phenyl-2-furyl)-2,4,6(1H,3H,5H)-pyrimidinetrione (0.7 g.) was dissolved in 15 ml. of 1 N sodium hydroxide, stirred at room temperature for 15 minutes, extracted with ethyl acetate, made slightly acidic with about 1 ml. of glacial acetic acid, and extracted with 25 ml. of ethyl acetate. The latter ethyl acetate extract was back washed with about 6.5 ml. of water, filtered over a bed of anhydrous magnesium sulfate and evaporated to yield solid 5-(5-phenyl-2-furyl)oxazolidine-2,4-dione [100 mg.; m.p. 216°-218° C.; Rf 0.6 (1:1 hexane:ethyl acetate/5% acetic acid)].

Workup

  1. extractionextracted with ethyl acetate
  2. extractionof glacial acetic acid, and extracted with 25 ml
  3. extractionThe latter ethyl acetate extract
  4. washwas back washed with about 6.5 ml
  5. filtrationof water, filtered over a bed of anhydrous magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-f401ed4edd144348bd8343151b827a28
Source dataset
uspto-grants-1984_06
Patent number
US04454320

Reaction notes

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