2-Phenylethanethioamide → Ethyl [(2-benzyl-4,5-dihydronaphtho[1,2-d]thiazol-6-yl)oxy]acetate

HRID 1067453

반응식

HRID 1067453 반응식
[CH2:1]([O:3][C:4](=[O:19])[CH2:5][O:6][C:7]1[C:16]2[CH2:15][CH2:14][CH:13](Br)[C:12](=O)[C:11]=2[CH:10]=[CH:9][CH:8]=1)[CH3:2].[C:20]1([CH2:26][C:27]([NH2:29])=[S:28])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(O)C.CN(C)C=O.O>[CH2:1]([O:3][C:4](=[O:19])[CH2:5][O:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[CH2:15][CH2:14][C:13]1[S:28][C:27]([CH2:26][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[N:29][C:12]=12)[CH3:2]

참가 물질

6

반응물 2

HCID 7313682-PhenylethanethioamideHCID 21193655Ethyl[(6-bromo-5,6,7,8-tetrahydro-5-oxo-1-naphthalenyl)oxy]acetate

생성물 1

HCID 86584198Ethyl [(2-benzyl-4,5-dihydronaphtho[1,2-d]thiazol-6-yl)oxy]acetate수율 21.5%

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

A solution of ethyl[(6-bromo-5,6,7,8-tetrahydro-5-oxo-1-naphthalenyl)oxy]acetate (2.16 g, 6.61 mmol) and phenylthioacetamide (1.00 g, 6.61 mmol) in a mixture of ethanol (25 mL) and N,N-dimethylformamide (5 mL) was stirred at 60° C. for 14 hours and, then, refluxed for 2 hours. After cooling, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride solution, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane-ethyl acetate=1:5) to provide ethyl[(2-benzyl-4,5-dihydronaphtho[1,2-d]thiazol-6-yl)oxy]acetate (540 mg). To a solution of this compound (0.54 g, 1.42 mmol) in a mixture of tetrahydrofuran (16 mL) and methanol (4 mL) was added 1N-hydrochloric acid followed by extraction with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride solution, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-hexane to provide 320 mg of the title compound. Yield 14%.

후처리

  1. temperaturerefluxed for 2 hours
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated aqueous sodium chloride solution
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-54ded62641cf4f2f8f7ae1f391d89c50
출처 데이터셋
uspto-grants-2001_06
특허 번호
US06248766B1

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