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

HRID 1504438Notes

Reaction equation

HRID 1504438 reaction equation
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

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

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

Workup

  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)

Sources & evidence

ORD record
ord-00ecb627abc941f6b4bd4f7ddc7d166b
Source dataset
uspto-grants-2015_12
Patent number
US09212182B2

Reaction notes

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