N-bromobutanimide → HCID 16064396, 화합물

HRID 2425514노트

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HRID 2425514 반응식
[CH3:1][C:2]1[C:3]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[N:4][C:5]2[C:10]([C:11]=1[C:12]([NH:14][C@H:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:16][CH3:17])=[O:13])=[CH:9][CH:8]=[CH:7][CH:6]=2.C1C(=O)N([Br:37])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:37][CH2:1][C:2]1[C:3]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[N:4][C:5]2[C:10]([C:11]=1[C:12]([NH:14][C@H:15]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[CH2:16][CH3:17])=[O:13])=[CH:9][CH:8]=[CH:7][CH:6]=2

참가 물질

4

반응물 2

HCID 67184N-bromobutanimide2회HCID 66040093-Methyl-2-phenyl-N-(1-phenylpropyl)quinoline-4-carboximidic acid

생성물 1

HCID 16064396HCID 16064396, 화합물수율 24.3%

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

실험 절차

3-methyl-2-phenyl-N-[(1S)-1-phenylpropyl]quinoline-4-carboxamide (9.8 g, 26 mmol) was dissolved in 200 mL hot CCl4 (with stirring) under N2 and heated at a gentle reflux. NBS (6.9 g, 39 mmol) was added and solution irradiated with long wave UV light for 0.5 h. Additional NBS (1.9 g, 11 mmol) was added and solution irradiated and refluxed for another 0.5 h. It was then allowed to cool and concentrated under reduced pressure to remove most of the CCl4. The residue was then dissolved in CH2Cl2 and washed with aqueous NaHCO3 containing a few crystals of sodium thiosulfate. The organic layer was then dried over Na2SO4, filtered, and concentrated under reduced pressure. The resulting material was then purified using silica gel chromatography (0-15% EtOAc/CH2Cl2) to give 2.9 g of desired product (24%) as a yellow-white solid. 1H NMR (300 MHz, CDCl3, 52° C.) δ 8.11 (d, J=8.1 Hz, 1H), 7.81-7.67 (m, 2H), 7.67-7.58 (m, 2H), 7.55-7.26 (m, 9H), 6.39 (d, J=7.8 Hz, 1H), 5.28 (q, J=7.6 Hz, 1H), 4.74-4.50 (m, 2H), 2.23-1.91 (m, 2H), 1.03 (t, J=7.4 Hz, 3H); LCMS: m/z 459 (MH+).

후처리

  1. temperatureheated at a gentle reflux
  2. customsolution irradiated with long wave UV light for 0.5 h
  3. customsolution irradiated
  4. temperaturerefluxed for another 0.5 h
  5. temperatureto cool
  6. concentrationconcentrated under reduced pressure
  7. customto remove most of the CCl4
  8. dissolutionThe residue was then dissolved in CH2Cl2
  9. washwashed with aqueous NaHCO3 containing a few crystals of sodium thiosulfate
  10. dry with materialThe organic layer was then dried over Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure
  13. customThe resulting material was then purified

출처 및 근거

ORD 기록
ord-0ff7fd02034c4d92aa67147e691bd84d
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07964733B2

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