Potassium Carbonate → 2-(4-(S-Methylsulfonimidoyl)benzyl)isoindoline-1,3-dione

HRID 527357Notes

Reaction equation

HRID 527357 reaction equation
C(=O)([O-])[O-].[K+].[K+].FC(F)(F)C([N:11]=[S:12]([C:15]1[CH:32]=[CH:31][C:18]([CH2:19][N:20]2[C:28](=[O:29])[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21]2=[O:30])=[CH:17][CH:16]=1)([CH3:14])=[O:13])=O>CO>[CH3:14][S:12]([C:15]1[CH:16]=[CH:17][C:18]([CH2:19][N:20]2[C:28](=[O:29])[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21]2=[O:30])=[CH:31][CH:32]=1)(=[NH:11])=[O:13]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 899785932-(4-(N-Trifluoracetyl-S-methylsulfonimidoyl)benzyl)isoindoline-1,3-dione

Product 1

HCID 867116292-(4-(S-Methylsulfonimidoyl)benzyl)isoindoline-1,3-dione

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium carbonate (3.37 g, 24.4 mmol) is added to a solution of 2-(4-(N-trifluoracetyl-S-methylsulfonimidoyl)benzyl)isoindoline-1,3-dione (preparation 17a, 2.00 g, 4.88 mmol) in methanol (20 mL). The mixture is stirred at room temperature for 16 h and filtered. The filtrate is concentrated under reduced pressure, and the residue is purified by flash chromatography on silica (methanol/dichloromethane 7:3). Yield: 0.90 g (58% of theory); ESI mass spectrum: [M+H]+=315, r.t. HPLC: 1.08 min (V003_003).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate is concentrated under reduced pressure
  3. customthe residue is purified by flash chromatography on silica (methanol/dichloromethane 7:3)
  4. custom=315, r.t
  5. custom1.08 min (V003_003)

Sources & evidence

ORD record
ord-11e4da07d7194013abf7390d33bed29d
Source dataset
uspto-grants-2016_05
Patent number
US09346794B1

Reaction notes

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