Lawesson's reagent → 7-bromo-4,5-dihydrospiro[benzo[b][1,4]diazepine-3,1'-cyclopropane]-2(1H)-thione

HRID 1485430Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1485430
[Br:1][C:2]1[CH:15]=[CH:14][C:5]2[NH:6][C:7](=O)[C:8]3([CH2:11][NH:12][C:4]=2[CH:3]=1)[CH2:10][CH2:9]3.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:25])=CC=1>O1CCCC1>[Br:1][C:2]1[CH:15]=[CH:14][C:5]2[NH:6][C:7](=[S:25])[C:8]3([CH2:11][NH:12][C:4]=2[CH:3]=1)[CH2:10][CH2:9]3

Komponenten

4

Edukt 2

HCID 87949Lawesson's reagentHCID 709789007-bromo-4,5-dihydrospiro[benzo[b][1,4]diazepine-3,1'-cyclopropan]-2(1H)-one

Produkt 1

HCID 867185037-bromo-4,5-dihydrospiro[benzo[b][1,4]diazepine-3,1'-cyclopropane]-2(1H)-thioneAusbeute 44,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 7-bromo-4,5-dihydrospiro[benzo[b][1,4]diazepine-3,1′-cyclopropan]-2(1H)-one (267 mg, 1.0 mmol) and Lawesson's reagent (606 mg, 1.5 mmol) in tetrahydrofuran (15 mL) was heated to 80° C., and maintained at the same temperature for 1 hours. The mixture was concentrated. To the residue was added water (50 mL), extracted with ethyl acetate (50 mL). The organic phase was washed with water (50 mL*2), dried by sodium sulfate, filtered and concentrated to give a residue. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=6:1) to afford 7-bromo-4,5-dihydrospiro[benzo[b][1,4]diazepine-3,1′-cyclopropane]-2(1H)-thione (125 mg, 44%).

Aufarbeitung

  1. temperaturemaintained at the same temperature for 1 hours
  2. concentrationThe mixture was concentrated
  3. additionTo the residue was added water (50 mL)
  4. extractionextracted with ethyl acetate (50 mL)
  5. washThe organic phase was washed with water (50 mL*2)
  6. dry with materialdried by sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a residue
  10. customThe residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=6:1)

Quellen und Nachweise

ORD-Eintrag
ord-d62d78ea428c41fe80dacecc2a5d6beb
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09422292B2

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