4-Aminothiophenol → 4-(4-Aminophenylthio)-7-trifluoromethylquinoline

HRID 55073

반응식

HRID 55073 반응식
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([F:15])([F:14])[F:13])=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[NH2:16][C:17]1[CH:22]=[CH:21][C:20]([SH:23])=[CH:19][CH:18]=1>CN(C)C1C=CN=CC=1.C(O)C>[NH2:16][C:17]1[CH:22]=[CH:21][C:20]([S:23][C:2]2[C:11]3[C:6](=[CH:7][C:8]([C:12]([F:15])([F:14])[F:13])=[CH:9][CH:10]=3)[N:5]=[CH:4][CH:3]=2)=[CH:19][CH:18]=1

참가 물질

5

반응물 2

HCID 145104-AminothiophenolHCID 676684-Chloro-7-(trifluoromethyl)quinoline

생성물 1

HCID 189716714-(4-Aminophenylthio)-7-trifluoromethylquinoline수율 74.1%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 702Ethanol용매

실험 절차

4-Chloro-7-trifluoromethylquinoline (0.043 moles, 10.0 g), 4-aminothiophenol (0.043 moles, 5.3 g) and 4-dimethylaminopyridine (0.04 moles, 4.9 g) were stirred in 250 ml ethanol for 3 days. The reaction mixture was filtered, concentrated, ethyl acetate added, washed with water and dried over sodium sulfate. The solution was concentrated and the product purified by HPLC over silica gel eluted with 25% ethyl acetate/hexane to yield 4-(4-aminophenylthio)-7-trifluoromethylquinoline 10.2 g, 74%. Mass Spec (FD) 320. Calculated for C16H11F3N2S: C, 59.99; H, 3.46; N, 8.74. Found: C, 60.08; H, 3.49; N, 8.77.

후처리

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. additionethyl acetate added
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationThe solution was concentrated
  7. customthe product purified by HPLC over silica gel
  8. washeluted with 25% ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-3f3c49436bc044d2a8d9d94e039ec63e
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05624937

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