Chloroacetone → HCID 13200304、化合物

HRID 1903230ノート

反応式

HRID 1903230 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](=[S:18])[NH:10][C:11]3[C:16]([CH:17]=2)=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:4][CH:3]=1.[H-].[Na+].[H][H].Cl[CH2:24][C:25](=[O:27])[CH3:26]>CN(C)C=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([S:18][CH2:24][C:25](=[O:27])[CH3:26])=[N:10][C:11]3[C:16]([CH:17]=2)=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 6571ChloroacetoneHCID 24758Sodium hydrideHCID 13200303HCID 13200303、化合物HCID 178418361HCID 178418361、化合物

生成物 1

HCID 13200304HCID 13200304、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

3-(p-Fluorophenyl)quinolin-2-thione (5.05 g.) was added in portions to a stirred suspension of sodium hydride (1.0 g. of a 50% w/w dispersion in mineral oil) in dimethylformamide (30 ml.) at 0°-5°. When all the hydrogen had evolved, chloroacetone (1.83 g.) was added and the mixture was stirred at ambient temperature for 18 hr. The mixture was poured into ice-water (300 ml.) and extracted with ethyl acetate (3×100 ml.). The ethyl acetate extract was washed with brine (75 ml.) and then dried (MgSO4). The solvent was evaporated and the residue was chromatographed on basic alumina (200 g., Brockmann Grade III), eluted with increasing concentrations of ethyl acetate in petroleum ether. The eluate obtained with 10% v/v ethyl acetate in petroleum ether was evaporated to give 3-(p-fluorophenyl)-2-(2-oxopropylthio)quinoline, m.p. 95°-96°.

後処理

  1. customat 0°-5°
  2. extractionextracted with ethyl acetate (3×100 ml.)
  3. extractionThe ethyl acetate extract
  4. washwas washed with brine (75 ml.)
  5. dry with materialdried (MgSO4)
  6. customThe solvent was evaporated
  7. customthe residue was chromatographed on basic alumina (200 g., Brockmann Grade III)
  8. washeluted
  9. temperaturewith increasing concentrations of ethyl acetate in petroleum ether
  10. customThe eluate obtained with 10% v/v ethyl acetate in petroleum ether
  11. customwas evaporated

出典と根拠

ORDレコード
ord-db94811dbfe248f99dd8df474cea72e2
出典データセット
uspto-grants-1984_03
特許番号
US04435405

反応ノート

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