Sodium hydrosulfide → 7-Ethoxyquinoline-4(1H)-thione

HRID 965005ノート

反応式

HRID 965005 の反応式
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH2:13][CH3:14])=[CH:9][CH:10]=2)[N:5]=[C:4](Br)[CH:3]=1.[SH-:16].[Na+]>CO>[CH2:13]([O:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2](=[S:16])[CH:3]=[CH:4][NH:5]2)=[CH:10][CH:9]=1)[CH3:14]

参加物

4

反応物 2

HCID 28015Sodium hydrosulfideHCID 19075044HCID 19075044、化合物

生成物 1

HCID 190750767-Ethoxyquinoline-4(1H)-thione収率 83%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

4-Chloro(bromo)-7-ethoxyquinoline (180 mg) and 70% sodium hydrosulfide (250 mg) were dissolved in methanol(50 ml) and refluxed for 15 hours. This reaction mixture was evaporated under reduced pressure and the residue was developed by silica gel column chromatography [Wako Gel™ C-200, mixed solution of methylene chloride with methanol (9 : 1)]. Fractions corresponding to yellow spots were collected and evaporated to obtain crude crystals. The obtained crude crystals were recrystallized from 40% aqueous ethanol solution to obtain 107 mg of the titled compound. Melting Point: 171°-174° C.; MS m/z: 205 (M+); NMR(DMSO-d6)δ: 1.40(3H, t, J=6.9 Hz), 4.15(2H, q, J=6.9 Hz), 7.02(1H, d, J=1.3 Hz), 7.09(1H, dd, J=2.3, 9.2 Hz), 7.15(1H, d, J=6.5 Hz), 7.73-7.78(1H, m), 8.58(1H, d, J=9.2 Hz), 12.68(1H, brs)

後処理

  1. temperaturerefluxed for 15 hours
  2. customThis reaction mixture was evaporated under reduced pressure
  3. additionthe residue was developed by silica gel column chromatography [Wako Gel™ C-200, mixed solution of methylene chloride with methanol (9 : 1)]
  4. customFractions corresponding to yellow spots were collected
  5. customevaporated
  6. customto obtain crude crystals
  7. customThe obtained crude crystals
  8. customwere recrystallized from 40% aqueous ethanol solution

出典と根拠

ORDレコード
ord-f967af128b16416e971d73ca0f925335
出典データセット
uspto-grants-1998_06
特許番号
US05773449

反応ノート

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