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m-Aminoacetanilide → N-(3-{[(7-{[(3-Hydroxyphenyl)amino]sulfonyl}-9-oxo-9H-fluoren-2-yl)sulfonyl]amino}phenyl)acetamide

HRID 2120916
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HRID 2120916 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[NH2:9][C:10]1[CH:11]=[C:12]([NH:16][C:17](=[O:19])[CH3:18])[CH:13]=[CH:14][CH:15]=1.[O:20]=[C:21]1[C:33]2[CH:32]=[C:31]([S:34](Cl)(=[O:36])=[O:35])[CH:30]=[CH:29][C:28]=2[C:27]2[C:22]1=[CH:23][C:24]([S:38](Cl)(=[O:40])=[O:39])=[CH:25][CH:26]=2>N1C=CC=CC=1>[OH:8][C:4]1[CH:3]=[C:2]([NH:1][S:34]([C:31]2[CH:32]=[C:33]3[C:28]([C:27]4[CH:26]=[CH:25][C:24]([S:38]([NH:9][C:10]5[CH:11]=[C:12]([NH:16][C:17](=[O:19])[CH3:18])[CH:13]=[CH:14][CH:15]=5)(=[O:39])=[O:40])=[CH:23][C:22]=4[C:21]3=[O:20])=[CH:29][CH:30]=2)(=[O:35])=[O:36])[CH:7]=[CH:6][CH:5]=1
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참가 물질

5

반응물 3

HCID 7604m-AminoacetanilideHCID 115683-AminophenolHCID 27945729-Oxo-9H-fluorene-2,7-disulfonyl dichloride

생성물 1

HCID 9985345N-(3-{[(7-{[(3-Hydroxyphenyl)amino]sulfonyl}-9-oxo-9H-fluoren-2-yl)sulfonyl]amino}phenyl)acetamide수율 39%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

3-Aminophenol (0.29 g, 2.65 mmmol) and N-(3-aminophenyl)acetamide (0.49 g, 2.65 mmol) in pyridine were treated with 9-oxo-9H-fluorene-2,7-disulfonyl dichloride (1.00 g, 2.65 mmol) in one portion at 0° C. The mixture was allowed to warm to ambient temperature and stirred for 1 hour after which the volatiles were evaporated under reduced pressure. The residue was partitioned between ethyl acetate and H2O. The separated organic phase was washed with 1N HCl, brine, dried (Na2SO4), filtered, and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography (85% ethyl acetate/hexanes) to provide the title compound as a yellow solid (577 mg, 39% yield). 1H NMR (300 MHz, DMSO-d6) δ 9.91 (bs, 1H), 9.47 (s, 1H), 7.9-8.1 (m, 6H), 7.48 (m, 1H), 7.26 bd, 1H), 7.12 (t, 1H), 6.99 (t, 1H), 6.75 (m, 1H), 6.58 (t, 1H), 6.52 (dd, 1H), 6.42 (dd, 1H), 1.98 (s, 3H); MS (ESI) 562 (M−H)−.

후처리

  1. customwere evaporated under reduced pressure
  2. customThe residue was partitioned between ethyl acetate and H2O
  3. washThe separated organic phase was washed with 1N HCl, brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under reduced pressure
  7. customThe residue was purified by flash chromatography (85% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-3e2601917769433cb56db3d368e6f642
출처 데이터셋
uspto-grants-2004_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06693136B1

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