1,3-Dichloro-5,5-dimethylhydantoin → HCID 86687568, compound

HRID 1473514Notes

Reaction equation

HRID 1473514 reaction equation
C(SC1C=C2C(C(Cl)=CC=N2)=CC=1F)C1C=CC=CC=1.ClN1C(C)(C)C(=O)N(Cl)C1=O.[Cl:32][C:33]1[C:42]2[C:37](=[CH:38][C:39]([S:44](Cl)(=[O:46])=[O:45])=[C:40]([F:43])[CH:41]=2)[N:36]=[CH:35][CH:34]=1.[F:48][C:49]1[C:54]([F:55])=[C:53]([F:56])[C:52]([F:57])=[C:51]([F:58])[C:50]=1[OH:59].C(N(CC)CC)C>CCOC(C)=O.O.C(O)(=O)C.C(#N)C>[Cl:32][C:33]1[C:42]2[C:37](=[CH:38][C:39]([S:44]([O:59][C:50]3[C:49]([F:48])=[C:54]([F:55])[C:53]([F:56])=[C:52]([F:57])[C:51]=3[F:58])(=[O:46])=[O:45])=[C:40]([F:43])[CH:41]=2)[N:36]=[CH:35][CH:34]=1

Participants

10

Reactant 5

HCID 83601,3-Dichloro-5,5-dimethylhydantoinHCID 8471TriethylamineHCID 13041PentafluorophenolHCID 86687567HCID 86687567, compoundHCID 86687569HCID 86687569, compound

Product 1

HCID 86687568HCID 86687568, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A round-bottom flask was charged with 7-(benzylthio)-4-chloro-6-fluoroquinoline (0.148 g, 0.487 mmol), acetonitrile (4.59 ml), acetic acid (0.172 ml), and water (0.115 ml), and after cooling the suspension in an ice bath for 10 minutes (material fell out of solution), 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione (0.192 g, 0.974 mmol) was added in one portion (mixture became homogeneous). After 1 h, conversion to 4-chloro-6-fluoroquinoline-7-sulfonyl chloride was observed (light yellow solution), and 2,3,4,5,6-pentafluorophenol (0.179 g, 0.974 mmol) was added, followed by drop wise addition of triethylamine (0.170 ml, 1.218 mmol). After 25 minutes, the mixture was diluted with EtOAc and washed with water and brine, and then dried over sodium sulfate. After filtration and concentration in vacuo, the material was purified via silica gel chromatography (12-g RediSep Gold column, eluting with 0-50% ethyl acetate in heptane) to yield perfluorophenyl 4-chloro-6-fluoroquinoline-7-sulfonate as a white solid. m/z (ESI) 428.1 (M+H)+.

Workup

  1. additionwas added in one portion (mixture became homogeneous)
  2. additionwas added
  3. waitAfter 25 minutes
  4. washwashed with water and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationAfter filtration and concentration in vacuo
  7. customthe material was purified via silica gel chromatography (12-g RediSep Gold column, eluting with 0-50% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-183f22dfa64b4c0ea7620c2dcef3d83c
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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