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N-Hydroxyphthalimide → 2-(cyclohexylmethoxy)-1H-isoindole-1,3(2H)-dione

HRID 29159
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HRID 29159 반응식
[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].C1CCN2C(=NCCC2)CC1.[CH:24]1([CH2:30]Br)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1>CN(C=O)C>[CH:24]1([CH2:30][O:1][N:2]2[C:3](=[O:12])[C:4]3[C:5](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]2=[O:7])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 10665N-HydroxyphthalimideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 137636Cyclohexane, (bromomethyl)-

생성물 1

HCID 140744162-(cyclohexylmethoxy)-1H-isoindole-1,3(2H)-dione

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
55 °C

실험 절차

N-hydroxylphthalimide (18.4 mmol, 3.0 g) was dissolved in anhydrous DMF (20 mL) under nitrogen. To the stirring solution, DBU (27.6 mmol, 4.13 mL) was injected followed by cyclohexylmethyl bromide (23.0 mmol, 3.21 mL) and the reaction was warmed to 55° C. After stirring for 15 hours, the reaction was cooled to room temperature and concentrated to a red oil. The reaction was partitioned between ethyl acetate and 1N HCl. The organic layer was washed with saturated aqueous sodium bicarbonate solution, brine and dried over magnesium sulfate. The solvent was removed under vacuum, and the crude product was triturated with hexanes providing 3.05 g (64%) of an off-white colored solid. H1-NMR (CDCl3): δ 7.80 (2H,m), 7.73(2H,m), 3.98 (2H,d), 2.03-1.65 (5H,m), 1.31-1.03 (6H,m).

후처리

  1. temperaturethe reaction was cooled to room temperature
  2. concentrationconcentrated to a red oil
  3. customThe reaction was partitioned between ethyl acetate and 1N HCl
  4. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution, brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was removed under vacuum
  7. customthe crude product was triturated with hexanes providing 3.05 g (64%) of an off-white colored solid

출처 및 근거

ORD 기록
ord-1f7bcc198d744108926d6cefdbfb57d4
출처 데이터셋
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07419967B2

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