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1,3-Dichloro-5,5-dimethylhydantoin → Perfluorophenyl 1-(5-bromo-2-methoxyphenyl)-2-oxo-1,2-dihydroquinoline-6-sulfonate

HRID 1504438
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1504438
C(S[C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]([C:19]1[CH:24]=[C:23]([Br:25])[CH:22]=[CH:21][C:20]=1[O:26][CH3:27])[C:14](=[O:28])[CH:13]=[CH:12]2)C1C=CC=CC=1.ClN1C(C)(C)C(=O)N(Cl)C1=O.[S:40](Cl)(Cl)(=[O:42])=[O:41].[F:45][C:46]1[C:51]([F:52])=[C:50]([F:53])[C:49]([F:54])=[C:48]([F:55])[C:47]=1[OH:56]>CC#N.CC(O)=O.O>[Br:25][C:23]1[CH:22]=[CH:21][C:20]([O:26][CH3:27])=[C:19]([N:15]2[C:16]3[C:11](=[CH:10][C:9]([S:40]([O:56][C:47]4[C:46]([F:45])=[C:51]([F:52])[C:50]([F:53])=[C:49]([F:54])[C:48]=4[F:55])(=[O:42])=[O:41])=[CH:18][CH:17]=3)[CH:12]=[CH:13][C:14]2=[O:28])[CH:24]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 83601,3-Dichloro-5,5-dimethylhydantoinHCID 13041PentafluorophenolHCID 24648Sulfuryl chlorideHCID 1177369896-(benzylthio)-1-(5-bromo-2-methoxyphenyl)quinolin-2(1H)-one

Produkt 1

HCID 117736973Perfluorophenyl 1-(5-bromo-2-methoxyphenyl)-2-oxo-1,2-dihydroquinoline-6-sulfonateAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel2×HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

6-(Benzylthio)-1-(5-bromo-2-methoxyphenyl)quinolin-2(1H)-one (5.48 g, 12.11 mmol) was diluted with MeCN (38.0 ml), AcOH (1.444 ml) and water (0.950 ml), and the mixture was cooled to 0° C. 1,3-Dichloro-5,5-dimethylimidazolidine-2,4-dione (3.58 g, 18.17 mmol) was added in portions and the reaction was stirred in the ice bath for 5 minutes until complete conversion to the sulfonyl chloride (reaction went from heterogeneous yellow mixture to yellow solution upon addition). With the solution at 0° C., 2,3,4,5,6-pentafluorophenol (2.68 g, 14.54 mmol) was added, followed by TEA (6.75 ml, 48.5 mmol), and the reaction was allowed to warm to RT for 20 min. Water was added and the organics were extracted with DCM (×3), followed by drying via phase separator. The organics were then concentrated in vacuo and purified via MPLC eluting with 0-100% ethyl acetate in heptanes (with 10% DCM additive) to yield perfluorophenyl 1-(5-bromo-2-methoxyphenyl)-2-oxo-1,2-dihydroquinoline-6-sulfonate (5.92 g, 10.27 mmol, 85% yield) as a white solid. MS (ESI, pos. ion) m/z: [M+1] 576.0

Aufarbeitung

  1. temperatureto warm to RT for 20 min
  2. extractionthe organics were extracted with DCM (×3)
  3. customby drying via phase separator
  4. concentrationThe organics were then concentrated in vacuo
  5. custompurified via MPLC
  6. washeluting with 0-100% ethyl acetate in heptanes (with 10% DCM additive)

Quellen und Nachweise

ORD-Eintrag
ord-00ecb627abc941f6b4bd4f7ddc7d166b
Quelldatensatz
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09212182B2

Notizen zur Reaktion

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