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

HRID 527370Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 527370
[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]

Komponenten

7

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6285Tetraethylammonium BromideKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel2×

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-a0f7276e433a4214b96eff22b06bdd39
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09346794B1

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