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

HRID 1473514노트

반응식

HRID 1473514 반응식
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

참가 물질

10

반응물 5

HCID 83601,3-Dichloro-5,5-dimethylhydantoinHCID 8471TriethylamineHCID 13041PentafluorophenolHCID 86687567HCID 86687567, 화합물HCID 86687569HCID 86687569, 화합물

생성물 1

HCID 86687568HCID 86687568, 화합물

시약·촉매·용매 4

HCID 176Acetic Acid용매HCID 962Water용매HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-183f22dfa64b4c0ea7620c2dcef3d83c
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09012443B2

반응 노트

불러오는 중…