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

HRID 55062

反応式

HRID 55062 の反応式
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

参加物

5

反応物 2

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

生成物 1

HCID 189716462-(4-Aminophenylthio)-4-ethoxycarbonylquinoline収率 36%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-603b04cd056d463f8fd093942204d27e
出典データセット
uspto-grants-1997_04
特許番号
US05624937

関連ノート

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