홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

1,3-Dichloro-5,5-dimethylhydantoin → Perfluorophenyl 8-(2-methoxy-4-(trifluoromethyl)phenyl)-1,7-naphthyridine-3-sulfonate

HRID 1473494
노트
인쇄 미리보기

반응식

HRID 1473494 반응식
C(S[C:9]1[CH:10]=[N:11][C:12]2[C:17]([CH:18]=1)=[CH:16][CH:15]=[N:14][C:13]=2[C:19]1[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][C:20]=1[O:29][CH3:30])C1C=CC=CC=1.ClN1C(C)(C)C(=O)N(Cl)C1=O.[S:42](Cl)(Cl)(=[O:44])=[O:43].[F:47][C:48]1[C:53]([F:54])=[C:52]([F:55])[C:51]([F:56])=[C:50]([F:57])[C:49]=1[OH:58].C(N(CC)CC)C>CCOC(C)=O.O.C(O)(=O)C.C(#N)C>[CH3:30][O:29][C:20]1[CH:21]=[C:22]([C:25]([F:27])([F:28])[F:26])[CH:23]=[CH:24][C:19]=1[C:13]1[N:14]=[CH:15][CH:16]=[C:17]2[C:12]=1[N:11]=[CH:10][C:9]([S:42]([O:58][C:49]1[C:48]([F:47])=[C:53]([F:54])[C:52]([F:55])=[C:51]([F:56])[C:50]=1[F:57])(=[O:44])=[O:43])=[CH:18]2
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

10

반응물 5

HCID 83601,3-Dichloro-5,5-dimethylhydantoinHCID 8471TriethylamineHCID 13041PentafluorophenolHCID 24648Sulfuryl chlorideHCID 866875483-(Benzylthio)-8-(2-methoxy-4-(trifluoromethyl)phenyl)-1,7-naphthyridine

생성물 1

HCID 86687549Perfluorophenyl 8-(2-methoxy-4-(trifluoromethyl)phenyl)-1,7-naphthyridine-3-sulfonate
수율 76%

시약·촉매·용매 4

HCID 176Acetic Acid용매HCID 962Water용매HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

실험 절차

To a vial charged with 3-(benzylthio)-8-(2-methoxy-4-(trifluoromethyl)phenyl)-1,7-naphthyridine (0.295 g, 0.692 mmol) was added acetonitrile (3.26 ml), acetic acid (0.122 ml) and water (0.081 ml). The resulting solution was cooled in an ice water bath prior to the addition of 1,3-dichloro-5,5-dimethylhydantoin (0.068 ml, 0.519 mmol). After 90 min of stirring (ice melt) LC/MS indicated fairly clean conversion to sulfonyl chloride. To the mixture was added 2,3,4,5,6-pentafluorophenol (0.036 ml, 0.346 mmol) followed by the drop wise addition of triethylamine (0.193 ml, 1.384 mmol). After 15 min LC/MS indicated complete conversion to product. The yellow solution was diluted with EtOAc and extracted with water. The aqueous phase was extracted with EtOAc and the combined organics were dried with Na2SO4, filtered, dried under reduced pressure and the crude oil purified with a 40 g silicycle HP column (SiliCycle, Inc. Quebec City, Canada) ramping EtOAc in heptane (0 to 65%, 5% DCM throughout) to afford perfluorophenyl 8-(2-methoxy-4-(trifluoromethyl)phenyl)-1,7-naphthyridine-3-sulfonate (0.145 g, 0.263 mmol, 76% yield) as a white foam. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.30 (s, 1H) 7.45 (dt, J=7.78, 0.81 Hz, 1H) 7.60-7.65 (m, 1H) 7.89 (d, J=5.77 Hz, 1H) 8.90 (d, J=2.35 Hz, 1H) 8.95 (d, J=5.58 Hz, 1H) 9.36 (d, J=2.35 Hz, 1H). m/z (ESI) 551.2 (M+H)+.

후처리

  1. temperatureThe resulting solution was cooled in an ice water bath
  2. waitAfter 15 min LC/MS indicated complete
  3. extractionextracted with water
  4. extractionThe aqueous phase was extracted with EtOAc
  5. dry with materialthe combined organics were dried with Na2SO4
  6. filtrationfiltered
  7. customdried under reduced pressure
  8. customthe crude oil purified with a 40 g silicycle HP column (SiliCycle, Inc. Quebec City, Canada)

출처 및 근거

ORD 기록
ord-16dab7c4f87c4c8d9fd55c10e88efbfa
출처 데이터셋
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09012443B2

반응 노트

불러오는 중…

이 페이지에서참가 물질실험 절차후처리출처 및 근거반응 노트