2-Naphthalenesulfonyl chloride → HCID 22351150, compound

HRID 896592Notes

Reaction equation

HRID 896592 reaction equation
[K].[CH3:2][C:3]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[NH:7][C:6](=[O:8])[NH:5][C:4]1=[O:9].[CH:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][C:17]=1[S:26](Cl)(=[O:28])=[O:27]>O1CCCC1>[CH3:2][C:3]1([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:7][C:6](=[O:8])[N:5]([S:26]([C:17]2[CH:18]=[CH:19][C:20]3[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:16]=2)(=[O:28])=[O:27])[C:4]1=[O:9]

Participants

4

Reactant 2

HCID 71252-Naphthalenesulfonyl chlorideHCID 69732011HCID 69732011, compound

Product 1

HCID 22351150HCID 22351150, compoundYield 14.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Methyl-5-phenylimidazolidine-2,4-dione potassium salt (1.00 g) was suspended in tetrahydrofuran (10 mL), 2-naphthalenesulfonyl chloride (1.02 g) was added slowly, and the mixture was stirred at room temperature overnight. After the solvent was distilled off, ethyl acetate (100 mL) was added to the reaction solution, and the solution was washed with 1N hydrochloric acid, an aqueous saturated sodium bicarbonate solution and a saturated brine in turn. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off. Further purification by silica gel chromatography (hexane:ethyl acetate=2:1) afforded 242 mg of white crystals.

Workup

  1. distillationAfter the solvent was distilled off
  2. additionethyl acetate (100 mL) was added to the reaction solution
  3. washthe solution was washed with 1N hydrochloric acid
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off
  6. customFurther purification by silica gel chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-a99c9db96da9443587ba70adae21fda1
Source dataset
uspto-grants-2005_07
Patent number
US06919365B2

Reaction notes

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