Benzyl Bromide → 1'-benzyl-2'-(benzylthio)-2-bromo-6,7-dihydro-5H-spiro[benzo[b]thiophene-4,4'-imidazol]-5'(1'H)-one

HRID 590528

반응식

HRID 590528 반응식
[Br:1][C:2]1[S:6][C:5]2[CH2:7][CH2:8][CH2:9][C:10]3([C:14](=[O:15])[NH:13][C:12](=[S:16])[NH:11]3)[C:4]=2[CH:3]=1.[H-].[Na+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1COCC1>[CH2:19]([N:13]1[C:14](=[O:15])[C:10]2([C:4]3[CH:3]=[C:2]([Br:1])[S:6][C:5]=3[CH2:7][CH2:8][CH2:9]2)[N:11]=[C:12]1[S:16][CH2:3][C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:5]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

참가 물질

5

반응물 3

HCID 7498Benzyl Bromide2회HCID 24758Sodium hydride2회HCID 900705422-bromo-2'-thioxo-6,7-dihydro-5H-spiro[benzo[b]thiophene-4,4'-imidazolidin]-5'-one

생성물 1

HCID 900705381'-benzyl-2'-(benzylthio)-2-bromo-6,7-dihydro-5H-spiro[benzo[b]thiophene-4,4'-imidazol]-5'(1'H)-one수율 111.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

2-Bromo-2′-thioxo-6,7-dihydro-5H-spiro[benzo[b]thiophene-4,4′-imidazolidin]-5′-one (0.285 g, 0.9 mmol) was dissolved in THF (20 mL) and cooled to 0° C. in an ice bath. Sodium hydride (50% dispersion in oil, 26 mg, 1.08 mmol) was added and the mixture was stirred for 15 min. Benzyl bromide (0.13 ml, 1.08 mmol) was added and the reaction mixture was stirred at room temperature for 1 h. The mixture was cooled to 0° C. again and a further portion of sodium hydride (50% dispersion in oil, 26 mg, 1.08 mmol) was added. The mixture was stirred for 15 min, benzyl bromide (0.13 mL, 1.08 mmol) was added and the reaction mixture was stirred at room temperature for 18 hr. Solvent was evaporated under reduced pressure. The residue was dissolved in water and extracted with dichloromethane (×3). The organic extracts were combined, dried (MgSO4), and concentrated in vacuo. The crude residue purified on silica gel using ethyl acetate in iso-hexane (1:1) to afford the title compound as a colourless oil (0.25 g, 56%).

후처리

  1. stirringthe reaction mixture was stirred at room temperature for 1 h
  2. temperatureThe mixture was cooled to 0° C. again
  3. stirringThe mixture was stirred for 15 min
  4. stirringthe reaction mixture was stirred at room temperature for 18 hr
  5. customSolvent was evaporated under reduced pressure
  6. dissolutionThe residue was dissolved in water
  7. extractionextracted with dichloromethane (×3)
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated in vacuo
  10. customThe crude residue purified on silica gel

출처 및 근거

ORD 기록
ord-8d9be4dcc75049c08f17f64ca6040f59
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09233982B2

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