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Water → N-2-(2-Furanyl)propenylphthalimide

HRID 256381
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인쇄 미리보기

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HRID 256381 반응식
ClN1[C:6](=O)[CH2:5][CH2:4][C:3]1=[O:8].[C:9]1([Se][Se]C2C=CC=CC=2)[CH:14]=CC=C[CH:10]=1.[C:23]1(=[O:33])[NH:27][C:26](=[O:28])[C:25]2=[CH:29][CH:30]=[CH:31][CH:32]=[C:24]12.[K].O>CN(C=O)C>[O:8]1[CH:3]=[CH:4][CH:5]=[C:6]1[C:9]([CH3:14])=[CH:10][N:27]1[C:23](=[O:33])[C:24]2=[CH:32][CH:31]=[CH:30][CH:29]=[C:25]2[C:26]1=[O:28]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 962WaterHCID 15460Diphenyl diselenideHCID 31398ChlorosuccinimideHCID 24194345Phthalimide potassium salt

생성물 1

HCID 53798517N-2-(2-Furanyl)propenylphthalimide수율 299.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

To a solution of 8.35 g (0.077 mole) of the olefin of Step A in 310 ml of DMF was added 12.37 g (0.093 mole) of N-chlorosuccinimide and 1.46 g (0.0047 mole) of diphenyl diselenide. After 3 hours at room temperature the mixture was partitioned between 500 ml of hexane and 1000 ml of 5% Na2S2O3. The hexane was distilled off at atmospheric pressure and the residue was dissolved in 200 ml of DMF, 9.49 g (0.051 mole) of potassium phthalimide was added and the mixture was warmed to 90° C. under N2. After 45 min. the cooled reaction mixture was poured into water and the precipitated product was filtered off and recrystallized from ethylacetate/2-propanol, affording 3.57 g colorless crystals, mp. 136°-137° C.

후처리

  1. customAfter 3 hours at room temperature the mixture was partitioned between 500 ml of hexane and 1000 ml of 5% Na2S2O3
  2. distillationThe hexane was distilled off at atmospheric pressure
  3. dissolutionthe residue was dissolved in 200 ml of DMF
  4. customAfter 45 min. the cooled reaction mixture
  5. filtrationthe precipitated product was filtered off
  6. customrecrystallized from ethylacetate/2-propanol

출처 및 근거

ORD 기록
ord-7c326113c7934c3eaca585bb14d50dfc
출처 데이터셋
uspto-grants-1987_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04703058

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