Water → 2-(4-(N-Cyanomethyl-S-methylsulfonimidoyl)benzyl)isoindoline-1,3-dione

HRID 527370Notes

Reaction equation

HRID 527370 reaction equation
[CH3:1][S:2]([C:5]1[CH:22]=[CH:21][C:8]([CH2:9][N:10]2[C:18](=[O:19])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]2=[O:20])=[CH:7][CH:6]=1)(=[NH:4])=[O:3].[H-].[K+].Br[CH2:26][C:27]#[N:28].O>COCCOC.[Br-].C([N+](CC)(CC)CC)C>[C:27]([CH2:26][N:4]=[S:2]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][N:10]2[C:18](=[O:19])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]2=[O:20])=[CH:21][CH:22]=1)([CH3:1])=[O:3])#[N:28]

Participants

7

Reactant 4

HCID 962WaterHCID 11534BromoacetonitrileHCID 82127Potassium hydrideHCID 867116292-(4-(S-Methylsulfonimidoyl)benzyl)isoindoline-1,3-dione

Product 1

HCID 867116382-(4-(N-Cyanomethyl-S-methylsulfonimidoyl)benzyl)isoindoline-1,3-dione

Reagents, catalysts & solvents 2

HCID 6285Tetraethylammonium BromideCatalystHCID 80711,2-DimethoxyethaneSolvent2×

Procedure

A mixture of 2-(4-(S-methylsulfonimidoyl)benzyl)isoindoline-1,3-dione (preparation 17b, 500 mg, 1.59 mmol) and 1,2-dimethoxyethane (2 mL) is added to a mixture of potassium hydride (30%, 260 mg, 1.95 mmol) in 1,2-dimethoxyethane (3 mL). The mixture is stirred for 15 min at room temperature and treated with tetraethylammonium bromide (10 mg, 0.05 mmol) and bromoacetonitrile (220 μL, 3.16 mmol). The mixture is heated at 110° C. over night and cooled to room temperature. Water is added, and the mixture is extracted twice with dichloromethane. The organic layer is concentrated under reduced pressure, and the residue is purified by flash chromatography on silica (gradient cyclohexane/ethyl acetate 1:0 to 0:1). Yield: 155 mg (27% of theory). ESI mass spectrum: [M+H]+=354; r.t. HPLC: 0.47 min (X011_S03).

Workup

  1. temperatureThe mixture is heated at 110° C. over night
  2. temperaturecooled to room temperature
  3. extractionthe mixture is extracted twice with dichloromethane
  4. concentrationThe organic layer is concentrated under reduced pressure
  5. customthe residue is purified by flash chromatography on silica (gradient cyclohexane/ethyl acetate 1:0 to 0:1)
  6. customr.t
  7. custom0.47 min (X011_S03)

Sources & evidence

ORD record
ord-a0f7276e433a4214b96eff22b06bdd39
Source dataset
uspto-grants-2016_05
Patent number
US09346794B1

Reaction notes

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