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

HRID 965005노트

반응식

HRID 965005 반응식
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]

참가 물질

4

반응물 2

HCID 28015Sodium hydrosulfideHCID 19075044HCID 19075044, 화합물

생성물 1

HCID 190750767-Ethoxyquinoline-4(1H)-thione수율 83%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-f967af128b16416e971d73ca0f925335
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05773449

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