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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
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2120916
[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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Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049
Pyridine
Lösungsmittel

Versuchsvorschrift

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)−.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-3e2601917769433cb56db3d368e6f642
Quelldatensatz
uspto-grants-2004_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06693136B1

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