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

HRID 1473411노트

반응식

HRID 1473411 반응식
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

참가 물질

10

반응물 5

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

생성물 1

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

시약·촉매·용매 4

HCID 176Acetic Acid용매HCID 962Water용매HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-4ac04802072c41d19d14b5badf83d476
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09012443B2

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