4-Aminothiophenol → 2-(4-Aminophenylthio)-4-ethoxycarbonylquinoline

HRID 55062

반응식

HRID 55062 반응식
Cl[C:2]1[CH:11]=[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH2:17][C:18]1[CH:23]=[CH:22][C:21]([SH:24])=[CH:20][CH:19]=1>CN(C)C1C=CN=CC=1.C(O)C>[NH2:17][C:18]1[CH:23]=[CH:22][C:21]([S:24][C:2]2[CH:11]=[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=2)=[CH:20][CH:19]=1

참가 물질

5

반응물 2

HCID 145104-AminothiophenolHCID 230586Ethyl 2-chloroquinoline-4-carboxylate

생성물 1

HCID 189716462-(4-Aminophenylthio)-4-ethoxycarbonylquinoline수율 36%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 702Ethanol용매

실험 절차

2-Chloro-4-ethoxycarbonylquinoline (0.024 moles, 5.56 g), 4-aminothiophenol (0.024 moles, 3.0 g) and 4-dimethylaminopyridine (0.024 moles, 2.9 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 2-(4-aminophenylthio)-4-ethoxycarbonylquinoline 2.8 g, 36%. Mass Spec (FD) 324. Calculated for C18H16N2O2S: C, 66.64; H, 4.97; N, 8.63. Found: C, 66.50; H, 5.00 N, 8.54.

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-603b04cd056d463f8fd093942204d27e
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05624937

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