m-Chloroperbenzoic acid → HCID 20244907, compound

HRID 482692Notes

Reaction equation

HRID 482692 reaction equation
[C:1]12([C:14](=[O:15])[NH:13][C:12](=[O:16])[NH:11]1)[C:10]1[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=1)[CH:4]=[CH:3][CH2:2]2.C(=O)(O)[O-:18].[Na+].ClC1C=CC=C(C(OO)=O)C=1>C(Cl)(Cl)Cl>[O:18]1[CH:4]2[CH:3]1[CH2:2][C:1]1([C:14](=[O:15])[NH:13][C:12](=[O:16])[NH:11]1)[C:10]1[C:5]2=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 20244915Spiro[imidazolidine-4,1′(2′H)-naphthalene]-2,5-dione

Product 1

HCID 20244907HCID 20244907, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a slurry of 2.7 g. (0.013 mole) of spiro[imidazolidine-4,1'(2'H)-naphthalene]-2,5-dione in 50 ml. of chloroform and 125 ml. of a 5% sodium bicarbonate solution was added 3.4 g. (0.016 mole) of m-chloroperbenzoic acid and the reaction mixture allowed to stir at room temperature for 3 hours. The reaction mixture was poured into 100 ml. of a 5% sodium bicarbonate solution and the product extracted with chloroform (2×75 ml.) and ethylacetate (2×75 ml.). The combined extracts were washed with a sodium bicarbonate solution and a brine solution, dried over sodium sulfate and concentrated to a yellow solid. Trituration with diethyl ether gave 1.6 g. (55% yield) of the desired product.

Workup

  1. additionThe reaction mixture was poured into 100 ml
  2. extractionof a 5% sodium bicarbonate solution and the product extracted with chloroform (2×75 ml.) and ethylacetate (2×75 ml.)
  3. washThe combined extracts were washed with a sodium bicarbonate solution
  4. dry with materiala brine solution, dried over sodium sulfate
  5. concentrationconcentrated to a yellow solid
  6. customTrituration with diethyl ether gave 1.6 g

Sources & evidence

ORD record
ord-5b8d0ad7e3014dcbbbe99abb9f471a3d
Source dataset
uspto-grants-1986_03
Patent number
US04575507

Reaction notes

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