Sodium Hydroxide → 5-(Thiophen-3-yl)-1,3-oxazolidine-2,4-dione

HRID 1262933Notes

Reaction equation

HRID 1262933 reaction equation
[OH:1][C:2]1([C:11]2[CH:15]=[CH:14][S:13][CH:12]=2)C(=O)N[C:5](=[O:9])[NH:4][C:3]1=[O:10].[OH-].[Na+]>C(O)(=O)C>[S:13]1[CH:14]=[CH:15][C:11]([CH:2]2[O:1][C:5](=[O:9])[NH:4][C:3]2=[O:10])=[CH:12]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 12962677HCID 12962677, compound

Product 1

HCID 129626215-(Thiophen-3-yl)-1,3-oxazolidine-2,4-dioneYield 51.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5-Hydroxy-5-(3-thienyl)-2,4,6(1H,3H,5H)pyrimidinetrione (1.16 g., 5.1 mmoles) was dissolved in 1 N sodium hydroxide (11 ml., 11 mmoles) and allowed to stand at room temperature for 15 minutes. The solution was acidified with acetic acid, and product allowed to crystallize over 35 minutes. Filtration gave 5-(3-thienyl)oxazolidine-2,4-dione (480 mg., 51%; m.p. 133°-135° C.). An additional crop of product was obtained by extracting the mother liquor with ethyl acetate. The extract was back washed with water, and evaporated to dryness (80 mg., contaminated with starting material).

Workup

  1. customto crystallize over 35 minutes
  2. filtrationFiltration

Sources & evidence

ORD record
ord-79b4e7caaa614cabb30119fe2948660c
Source dataset
uspto-grants-1984_06
Patent number
US04454320

Reaction notes

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