Methyl iodide → 2-[1-(Dimethylcarbamoyl)ethylthio]-3-phenylquinoline

HRID 1903218노트

반응식

HRID 1903218 반응식
[CH:1]([N-]C(C)C)(C)C.[Li+].C(NC(C)C)(C)C.C([Li])CCC.[CH3:21][N:22]([CH3:43])[C:23]([CH2:25][S:26][C:27]1[C:36]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[CH:35][C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:28]=1)=[O:24].IC>CCCCCC.O1CCCC1.O.C(O)(=O)C>[CH3:21][N:22]([CH3:43])[C:23]([CH:25]([S:26][C:27]1[C:36]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[CH:35][C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:28]=1)[CH3:1])=[O:24]

참가 물질

10

반응물 5

HCID 6328Methyl iodideHCID 7912DiisopropylamineHCID 2724682Lithium diisopropylamideHCID 204682172-(Dimethylcarbamoylmethylthio)-3-phenylquinolineHCID 178418339Butyllithium

생성물 1

HCID 132002102-[1-(Dimethylcarbamoyl)ethylthio]-3-phenylquinoline

시약·촉매·용매 4

HCID 176Acetic Acid용매HCID 962Water용매HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

실험 절차

To a solution of lithium di-isopropylamide [prepared from di-isopropylamine (6.2 ml.) and n-butyllithium (24.7 ml. of a 1.7 M solution in hexane) in dry tetrahydrofuran (100 ml.) at -78°. under argon] was added a solution of 2-(dimethylcarbamoylmethylthio)-3-phenylquinoline (6.6 g.) in dry tetrahydrofuran (50 ml.) at -60°. The mixture was then stirred for 15 min. at -60°. Iodomethane (2.7 ml.) was added and the mixture was allowed to warm up to ambient temperature. Glacial acetic acid (2.6 ml.) was then added, followed by water (200 ml.). The tetrahydrofuran phase was separated and retained, and the aqueous layer was extracted with ethyl acetate (2×30 ml.). The ethyl acetate and tetrahydrofuran phases were combined and dried (MgSO4). The solvent was evaporated and the residual oil was chromatographed on basic alumina (100 g. of Brockmann grade III) eluted with increasing concentrations of chloroform in petroleum ether. The eluate obtained with 20% v/v chloroform in petroleum ether on evaporation gave 2-[1-(dimethylcarbamoyl)ethylthio]-3-phenylquinoline as a viscous oil, which was used without further purification.

후처리

  1. customat -78°
  2. customThe tetrahydrofuran phase was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate (2×30 ml.)
  4. dry with materialdried (MgSO4)
  5. customThe solvent was evaporated
  6. customthe residual oil was chromatographed on basic alumina (100 g. of Brockmann grade III)
  7. washeluted
  8. temperaturewith increasing concentrations of chloroform in petroleum ether
  9. customThe eluate obtained with 20% v/v chloroform in petroleum ether on evaporation

출처 및 근거

ORD 기록
ord-34d005306b4a4c3a809703d81834c081
출처 데이터셋
uspto-grants-1984_03
특허 번호
US04435405

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