Sodium Hydroxide → HCID 12962670, compound

HRID 1262931Notes

Reaction equation

HRID 1262931 reaction equation
[OH:1][C:2]1([C:11]2[O:12][C:13]([CH3:16])=[CH:14][CH:15]=2)C(=O)N[C:5](=[O:9])[NH:4][C:3]1=[O:10].[OH-].[Na+]>>[CH3:16][C:13]1[O:12][C:11]([CH:2]2[O:1][C:5](=[O:9])[NH:4][C:3]2=[O:10])=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 12962669HCID 12962669, compound

Product 1

HCID 12962670HCID 12962670, compound

Procedure

5-Hydroxy-5-(5-methyl-2-furyl)-2,4,6(1H,3H,5H)-pyrimidinetrione (6.3 g.) was dissolved in 50 ml. of 1 N sodium hydroxide and stirred at room temperature for 15 minutes. The reaction mixture was extracted with 50 ml. of ethyl acetate, and acidified with glacial acetic acid. Product was then extracted into fresh ethyl acetate (three 30 ml. portions). The combined ethyl acetate extracts were filtered through a bed of anhydrous magnesium sulfate and evaporated to an oil. The oil was chromatographed on 50 ml. of silica gel, with 1:1 hexane:ethyl acetate/5% acetic acid as eluant. The column was monitored by tlc using the same eluant. Clean product containing fractions were combined, evaporated to dryness and triturated with hexane (311 mg., m.p. 135°-138° C.). Recrystallization from methanol/water afforded purified 5-(5-methyl-2-furyl)oxazolidine-2,4-dione (142 mg., m.p. 136.5°-137.5° C.).

Workup

  1. extractionThe reaction mixture was extracted with 50 ml
  2. extractionProduct was then extracted into fresh ethyl acetate (three 30 ml. portions)
  3. filtrationThe combined ethyl acetate extracts were filtered through a bed of anhydrous magnesium sulfate
  4. customevaporated to an oil
  5. customThe oil was chromatographed on 50 ml
  6. additioncontaining fractions
  7. customevaporated to dryness
  8. customtriturated with hexane (311 mg., m.p. 135°-138° C.)
  9. customRecrystallization from methanol/water
  10. customafforded
  11. custompurified 5-(5-methyl-2-furyl)oxazolidine-2,4-dione (142 mg., m.p. 136.5°-137.5° C.)

Sources & evidence

ORD record
ord-bb3ca84b4048451494e5cf907fbb19e9
Source dataset
uspto-grants-1984_06
Patent number
US04454320

Reaction notes

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