m-Chloroperbenzoic acid → HCID 13644522, compound

HRID 482689Notes

Reaction equation

HRID 482689 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH2:8][C:9]32[C:15](=[O:16])[NH:14][C:13](=[O:17])[NH:12]3)=[CH:4][CH:3]=1.C(=O)(O)[O-:19].[Na+].ClC1C=CC=C(C(OO)=O)C=1>C(Cl)(Cl)Cl>[O:19]1[CH:6]2[CH:7]1[CH2:8][C:9]1([C:15](=[O:16])[NH:14][C:13](=[O:17])[NH:12]1)[C:10]1[C:5]2=[CH:4][CH:3]=[C:2]([F:1])[CH:11]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acid2×HCID 516892Sodium BicarbonateHCID 13644521HCID 13644521, compound

Product 1

HCID 13644522HCID 13644522, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a slurry of 2.6 g. (0.011 mole) of 7'-fluorospiro[imidazolidine-4,1'(2'H)-naphthalene]2,5-dione in 50 ml. of chloroform was added 125 ml. of a 5% sodium bicarbonate solution followed by 3.0 g. (0.014 mole) of m-chloroperbenzoic acid. The reaction mixture was allowed to stir at room temperature for 4 hours after which an additional 1.2 g. (0.0055 mole) of m-chloroperbenzoic acid were added. After stirring overnight at room temperature the mixture was poured into 100 ml. of a 5% sodium bicarbonate solution and the mixture extracted (2×100 ml.) with chloroform and then with ethyl acetate (2×100 ml.). The organic extracts were combined, washed with water and a brine solution and dried over magnesium sulfate. Removal of the solvent gave 600 mg. (22% yield) of the desired product.

Workup

  1. stirringAfter stirring overnight at room temperature the mixture
  2. additionwas poured into 100 ml
  3. extractionof a 5% sodium bicarbonate solution and the mixture extracted (2×100 ml.) with chloroform
  4. washwashed with water
  5. dry with materiala brine solution and dried over magnesium sulfate
  6. customRemoval of the solvent
  7. customgave 600 mg

Sources & evidence

ORD record
ord-e353d1c4b7484083add03e49db4d1ed4
Source dataset
uspto-grants-1986_03
Patent number
US04575507

Reaction notes

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