Chloroacetone → HCID 13200304, 화합물

HRID 1903230노트

반응식

HRID 1903230 반응식
[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

참가 물질

6

반응물 4

HCID 6571ChloroacetoneHCID 24758Sodium hydrideHCID 13200303HCID 13200303, 화합물HCID 178418361HCID 178418361, 화합물

생성물 1

HCID 13200304HCID 13200304, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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°.

후처리

  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

출처 및 근거

ORD 기록
ord-db94811dbfe248f99dd8df474cea72e2
출처 데이터셋
uspto-grants-1984_03
특허 번호
US04435405

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