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

HRID 1473411ノート

反応式

HRID 1473411 の反応式
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

参加物

10

反応物 5

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

生成物 1

HCID 86687458Perfluorophenyl 4-chloroquinoline-7-sulfonate収率 100%

試薬・触媒・溶媒 4

HCID 176Acetic Acid溶媒HCID 962Water溶媒HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-4ac04802072c41d19d14b5badf83d476
出典データセット
uspto-grants-2015_04
特許番号
US09012443B2

反応ノート

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