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

HRID 527370ノート

反応式

HRID 527370 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6285Tetraethylammonium Bromide触媒HCID 80711,2-Dimethoxyethane溶媒2 回

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-a0f7276e433a4214b96eff22b06bdd39
出典データセット
uspto-grants-2016_05
特許番号
US09346794B1

反応ノート

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