Potassium Carbonate → 2-(4-(N-cyano-S-methylsulfonimidoyl)benzyl)isoindoline-1,3-dione

HRID 527342Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 527342
[C:1]([N:3]=[S:4]([C:6]1[CH:23]=[CH:22][C:9]([CH2:10][N:11]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]2=[O:21])=[CH:8][CH:7]=1)[CH3:5])#[N:2].C(=O)([O-])[O-:25].[K+].[K+].ClC1C=C(C=CC=1)C(OO)=O.[O-]S([O-])(=S)=O.[Na+].[Na+]>C(O)C>[C:1]([N:3]=[S:4]([C:6]1[CH:23]=[CH:22][C:9]([CH2:10][N:11]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]2=[O:21])=[CH:8][CH:7]=1)([CH3:5])=[O:25])#[N:2]

Komponenten

6

Edukt 4

HCID 11430Potassium CarbonateHCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acid2×HCID 867116092-(4-(N-cyano-S-methylsulfinimidoyl)benzyl)isoindoline-1,3-dione

Produkt 1

HCID 867116102-(4-(N-cyano-S-methylsulfonimidoyl)benzyl)isoindoline-1,3-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 2-(4-(N-cyano-S-methylsulfinimidoyl)benzyl)isoindoline-1,3-dione (preparation 6b, 5.75 g, 17.78 mmol) and potassium carbonate (7.37 g, 53.34 mmol) in ethanol (130 mL) is cooled at 0° C. and treated with meta-chloroperoxybenzoic acid (mCPBA, 5.98 g, 26.67 mmol). The reaction mixture is warmed to room temperature and stirred overnight before more mCPBA (2.39 g, 10.66 mmol) is added and the mixture is stirred for 4 h. Saturated aqueous Na2S2O3 solution is added, and the mixture is extracted twice with dichloromethane. The combined organic layers are dried over Na2SO4 and concentrated under reduced pressure. The residue is purified by flash chromatography on silica (gradient cyclohexane/ethyl acetate 1:1 to ethyl acetate). Yield: 2.47 g (41% of theory); ESI mass spectrum: [M+H]+=334; r.t. HPLC: 1.02 min (V003_003).

Aufarbeitung

  1. additionis added
  2. extractionthe mixture is extracted twice with dichloromethane
  3. dry with materialThe combined organic layers are dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by flash chromatography on silica (gradient cyclohexane/ethyl acetate 1:1 to ethyl acetate)
  6. customr.t
  7. custom1.02 min (V003_003)

Quellen und Nachweise

ORD-Eintrag
ord-95661767dadd44279e4afa9461e1b410
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09346794B1

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