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

HRID 527342Notes

Reaction equation

HRID 527342 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-95661767dadd44279e4afa9461e1b410
Source dataset
uspto-grants-2016_05
Patent number
US09346794B1

Reaction notes

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