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

Reaktionsgleichung

Reaktionsgleichung von HRID 590528
[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

Komponenten

5

Edukt 3

HCID 7498Benzyl Bromide2×HCID 24758Sodium hydride2×HCID 900705422-bromo-2'-thioxo-6,7-dihydro-5H-spiro[benzo[b]thiophene-4,4'-imidazolidin]-5'-one

Produkt 1

HCID 900705381'-benzyl-2'-(benzylthio)-2-bromo-6,7-dihydro-5H-spiro[benzo[b]thiophene-4,4'-imidazol]-5'(1'H)-oneAusbeute 111,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-8d9be4dcc75049c08f17f64ca6040f59
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09233982B2

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