1,3-Dichloro-5,5-dimethylhydantoin → HCID 86687568、化合物

HRID 1473514ノート

反応式

HRID 1473514 の反応式
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

参加物

10

反応物 5

HCID 83601,3-Dichloro-5,5-dimethylhydantoinHCID 8471TriethylamineHCID 13041PentafluorophenolHCID 86687567HCID 86687567、化合物HCID 86687569HCID 86687569、化合物

生成物 1

HCID 86687568HCID 86687568、化合物

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-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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-183f22dfa64b4c0ea7620c2dcef3d83c
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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