Potassium Iodide → 3-(4-Chlorophenyl)-5-iodo-5-methyl-oxazolidine-2,4-dione

HRID 26467Notes

Reaction equation

HRID 26467 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[C:11](Br)([CH3:14])[O:10][C:9]2=[O:16])=[CH:4][CH:3]=1.[I-:17].[K+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[C:11]([I:17])([CH3:14])[O:10][C:9]2=[O:16])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 4875Potassium IodideHCID 213237073-(4-Chlorophenyl)-5-bromo-5-methyl-oxazolidine-2,4-dione

Product 1

HCID 213237083-(4-Chlorophenyl)-5-iodo-5-methyl-oxazolidine-2,4-dione

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

6.1 g (0.02 mole) of the 3-(4-chlorophenyl)-5-bromo-5-methyl-oxazolidine-2,4-dione, produced in a manner analogous to that described in Example 1, and 33.2 g (0.2 mole) of potassium iodide are placed, together with a spatula tip of benzyltriethylammonium chloride, in 50 ml of water, and the mixture is stirred at 50° for 7 days. It is then cooled to room temperature, and the solid product is filtered off with suction. After washing with water, the crude product is taken up in methylene chloride, and extracted once with water. The organic phase is then dried over sodium sulphate, filtered, and concentrated in a vacuum evaporator. The substance remaining behind is digested with a small amount of ether/petroleum ether, then filtered off with suction and dried. There is obtained a yield of 3.3 g of substance having a melting point of 132°-142°.

Workup

  1. filtrationthe solid product is filtered off with suction
  2. washAfter washing with water
  3. extractionextracted once with water
  4. dry with materialThe organic phase is then dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated in a vacuum evaporator
  7. filtrationfiltered off with suction
  8. customdried
  9. customThere is obtained a yield of 3.3 g of substance

Sources & evidence

ORD record
ord-ea6bdc68b4f04cdbad0f3478d9dc9e09
Source dataset
uspto-grants-1979_04
Patent number
US04150144

Reaction notes

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