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

HRID 527342ノート

反応式

HRID 527342 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-95661767dadd44279e4afa9461e1b410
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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