Iodine → 3-iodo-4,5-dihydro-1H-benzo[b]azepin-2(3H)-one

HRID 1456630

Reaktionsgleichung

Reaktionsgleichung von HRID 1456630
[NH:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH2:5][CH2:4][CH2:3][C:2]1=[O:12].C[Si](C)(C)N[Si](C)(C)C.[I:22]I.S([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl.O>[I:22][CH:3]1[CH2:4][CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[NH:1][C:2]1=[O:12]

Komponenten

7

Edukt 4

HCID 807IodineHCID 13838HexamethyldisilazaneHCID 24437Sodium SulfiteHCID 2485801,3,4,5-Tetrahydro-2H-1-benzazepin-2-one

Produkt 1

HCID 110334773-iodo-4,5-dihydro-1H-benzo[b]azepin-2(3H)-oneAusbeute 60,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
30 °C

Versuchsvorschrift

A suspension of 34.2 g (212 mmol) of 2,3,4,5tetrahydro-1H-[1]-benzazapin-2-one and 224 mL (171.2 g, 1.06 mol) of hexamethyldisilazane in 400 mL of methylene chloride was heated at reflux for 15 min and cooled to 30° C. Iodine (161.5 g, 636 mmol) was added in one portion, the solution heated at reflux for 2.5 h, cooled, and poured into a 0° C. solution of 88.6 g of sodium sulfite in 800 mL of water, with vigorous stirring. The aqueous phase was separated, extracted with methylene choride and the combined organics were washed with water and concentrated in vacuo to approximately 200 mL. Toluene (800 mL) was added, the solution was concentrated to a slurry, and the product collected on a filter. Drying under vacuum gave 36.7 g (60%) of a tan powder. 1H NMR (300 MHz, CDCl3) d 8.47 (1H, bs), 7.3-7.1 (3H, m), 7.06 (1H, d, J=8 Hz), 4.68 (1H, t, J=8.7 Hz), 2.97 (1H, m), 2.80-2.60 (3H, m).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 15 min
  3. temperaturethe solution heated
  4. temperatureat reflux for 2.5 h
  5. temperaturecooled
  6. customThe aqueous phase was separated
  7. extractionextracted with methylene choride
  8. washthe combined organics were washed with water
  9. concentrationconcentrated in vacuo to approximately 200 mL
  10. additionToluene (800 mL) was added
  11. concentrationthe solution was concentrated to a slurry
  12. customthe product collected on a filter
  13. customDrying under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-d52a91c7557044248d135109a34e5900
Quelldatensatz
uspto-grants-1998_12
Patentnummer
US05843941

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