Cyclohexyl bromide → N-cyclohexyloxyphthalimide

HRID 29168

반응식

HRID 29168 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].[CH2:13]1[CH2:23][CH2:22]N2[C:16](=NCCC2)[CH2:15][CH2:14]1.C1(Br)CCCCC1>CN(C=O)C>[CH:13]1([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])[CH2:14][CH2:15][CH2:16][CH2:22][CH2:23]1

참가 물질

5

반응물 3

HCID 7960Cyclohexyl bromideHCID 10665N-HydroxyphthalimideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

생성물 1

HCID 10467039N-cyclohexyloxyphthalimide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
55 °C

실험 절차

N-hydroxylphthalimide (61.3 mmol, 10.0 g) was dissolved in anhydrous DMF (60 mL) under nitrogen. To the stirring solution, DBU (92.0 mmol, 13.75 mL) was injected followed by cyclohexyl bromide (76.6 mmol, 9.43 mL) and the reaction was warmed to 55° C. After stirring for 15 hours, the reaction was warmed to 80° C. for 5 hours, then 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 1N NaOH, brine and dried over magnesium sulfate. The solvent was removed under vacuum and the crude product was triturated with hexanes providing 2.89 g (19%) of a yellow solid. Rf: 0.7 (2:1 hexanes/ethyl acetate); H1-NMR (CDCl3): δ 7.80 (2H,m), 7.73(2H,m), 4.21 (1H,m), 2.02-1.98 (2H,m), 1.87-1.82 (2H,m), 1.59-1.53 (4H,m), 1.30-1.24 (2H,m).

후처리

  1. temperaturethe reaction was warmed to 80° C. for 5 hours
  2. temperaturecooled to room temperature
  3. concentrationconcentrated to a red oil
  4. customThe reaction was partitioned between ethyl acetate and 1N HCl
  5. washThe organic layer was washed with 1N NaOH, brine
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was removed under vacuum
  8. customthe crude product was triturated with hexanes providing 2.89 g (19%) of a yellow solid

출처 및 근거

ORD 기록
ord-16dd12d525704f8bb2157302ec748a15
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07419967B2

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