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

HRID 527342노트

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HRID 527342 반응식
[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]

참가 물질

6

반응물 4

HCID 11430Potassium CarbonateHCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acid2회HCID 867116092-(4-(N-cyano-S-methylsulfinimidoyl)benzyl)isoindoline-1,3-dione

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-95661767dadd44279e4afa9461e1b410
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346794B1

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