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Water → 5-Oxo-2,3,4,5-tetrahydro-1-benzothiepine-8-carbonitrile

HRID 585728
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 585728
Br[C:2]1[CH:13]=[CH:12][C:5]2[C:6](=[O:11])[CH2:7][CH2:8][CH2:9][S:10][C:4]=2[CH:3]=1.O.C(OCC)(=O)C.[CH3:21][N:22](C)C=O>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[O:11]=[C:6]1[C:5]2[CH:12]=[CH:13][C:2]([C:21]#[N:22])=[CH:3][C:4]=2[S:10][CH2:9][CH2:8][CH2:7]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 962WaterHCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 223374568-bromo-3,4-dihydro-2H-benzo[b]thiepin-5-one

Produkt 1

HCID 223374185-Oxo-2,3,4,5-tetrahydro-1-benzothiepine-8-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11186
Zinc cyanide (Zn(CN)2)
Katalysator
HCID 178418397HCID 178418397, VerbindungKatalysator

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

To a solution of 8-bromo-5-oxo-2,3,4,5-tetrahydro-1-benzothiepine (5.00 g) synthesized according to a known method in N,N-dimethylformamide (50 ml) were added zinc cyanide (2.28 g) and tetrakis(triphenylphosphine)palladium(0) (1.13 g) and the mixture was stirred at 80-90° C. for 1 hr. The reaction mixture was allowed to warm to room temperature and water (500 ml) and ethyl acetate (100 ml) were added. The mixture was passed through celite. The filtrate was extracted with ethyl acetate and the organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was concentrated under reduced pressure and the obtained residue was recrystallized from ethyl acetate and hexane to give the objective 5-oxo-2,3,4,5-tetrahydro-1-benzothiepine-8-carbonitrile (3.37 g) as pale yellow crystals.

Aufarbeitung

  1. temperatureto warm to room temperature
  2. extractionThe filtrate was extracted with ethyl acetate
  3. washthe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationThe solvent was concentrated under reduced pressure
  6. customthe obtained residue was recrystallized from ethyl acetate and hexane

Quellen und Nachweise

ORD-Eintrag
ord-9e07f701113149388ba08da50356ad64
Quelldatensatz
uspto-grants-2005_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06933305B2

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