1,3-Dichloro-5,5-dimethylhydantoin → Perfluorophenyl 4-chloroquinoline-7-sulfonate

HRID 1473411Notes

Reaction equation

HRID 1473411 reaction equation
C(SC1C=C2C(C(Cl)=CC=N2)=CC=1)C1C=CC=CC=1.ClN1C(C)(C)C(=O)N(Cl)C1=O.[Cl:31][C:32]1[C:41]2[C:36](=[CH:37][C:38]([S:42](Cl)(=[O:44])=[O:43])=[CH:39][CH:40]=2)[N:35]=[CH:34][CH:33]=1.[F:46][C:47]1[C:52]([F:53])=[C:51]([F:54])[C:50]([F:55])=[C:49]([F:56])[C:48]=1[OH:57].C(N(CC)CC)C>CCOC(C)=O.O.C(O)(=O)C.C(#N)C>[Cl:31][C:32]1[C:41]2[C:36](=[CH:37][C:38]([S:42]([O:57][C:48]3[C:47]([F:46])=[C:52]([F:53])[C:51]([F:54])=[C:50]([F:55])[C:49]=3[F:56])(=[O:43])=[O:44])=[CH:39][CH:40]=2)[N:35]=[CH:34][CH:33]=1

Participants

10

Reactant 5

HCID 83601,3-Dichloro-5,5-dimethylhydantoinHCID 8471TriethylamineHCID 13041PentafluorophenolHCID 866874577-(Benzylthio)-4-chloroquinolineHCID 866874594-Chloroquinoline-7-sulfonyl chloride

Product 1

HCID 86687458Perfluorophenyl 4-chloroquinoline-7-sulfonateYield 100%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A round-bottom flask was charged with 7-(benzylthio)-4-chloroquinoline (7.35 g, 25.7 mmol), acetonitrile (242 ml), acetic acid (9.08 ml), and water (6.05 ml), and after cooling the suspension in an ice bath for 10 minutes, 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione (10.13 g, 51.4 mmol) was added in one portion to form a heterogeneous solution. After 20 minutes, conversion to 4-chloroquinoline-7-sulfonyl chloride was observed, and 2,3,4,5,6-pentafluorophenol (9.47 g, 51.4 mmol) was added, followed by drop wise addition of triethylamine (8.96 ml, 64.3 mmol). After 40 minutes, the mixture was diluted with EtOAc (200 mL) and washed with water (2×200 mL) and brine, and then dried over sodium sulfate. After filtration and concentration under a vacuum, the material was purified via silica gel chromatography (120-g column) eluting with 0 to 35% ethyl acetate in heptane to yield perfluorophenyl 4-chloroquinoline-7-sulfonate (10.54 g, 25.7 mmol, 100% yield) as a light yellow oily solid. m/z (ESI) 410.1 (M+H)+.

Workup

  1. temperatureafter cooling the suspension in an ice bath for 10 minutes
  2. customto form a heterogeneous solution
  3. waitAfter 40 minutes
  4. washwashed with water (2×200 mL) and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationAfter filtration and concentration under a vacuum
  7. customthe material was purified via silica gel chromatography (120-g column)
  8. washeluting with 0 to 35% ethyl acetate in heptane

Sources & evidence

ORD record
ord-4ac04802072c41d19d14b5badf83d476
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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