Dibromomethane → 3-(2-[1,3]Dithietan-2-ylidene-2-pyridin-4-yl-acetyl)-benzonitrile

HRID 38087

Reaktionsgleichung

Reaktionsgleichung von HRID 38087
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][C:8]([C:10]2[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=2)[C:13]#[N:14])=[O:9])=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[C:24](=[S:26])=[S:25].Br[CH2:28]Br>CS(C)=O.O>[S:25]1[CH2:28][S:26][C:24]1=[C:7]([C:4]1[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=1)[C:8]([C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=1)[C:13]#[N:14])=[O:9]

Komponenten

7

Edukt 4

HCID 3024DibromomethaneHCID 6348Carbon DisulfideHCID 11430Potassium CarbonateHCID 671843533-(Pyridin-4-yl-acetyl)-benzonitrile

Produkt 1

HCID 229441233-(2-[1,3]Dithietan-2-ylidene-2-pyridin-4-yl-acetyl)-benzonitrileAusbeute 58,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 3-(pyridin-4-yl-acetyl)-benzonitrile (12.5 g, 56 mmol) in dry DMSO (280 mL) under nitrogen atmosphere solid potassium carbonate (23.36 g, 169 mmol, 3 eq) was added at room temperature, followed by carbon disulfide (10.2 mL, 169 mmol, 3 eq) and dibromomethane (11.86 mL, 169 mmol, 3 eq). The reaction mixture was stirred at room temperature for 2 hours and then poured into stirred iced water (1.5 L mL). The orange precipitate was filtered, washed with water and dried at 60° C. under reduced pressure for 1 hour. The crude product was purified by silica gel chromatography (SP1, eluant: n-hexane/ethyl acetate 2:8) to obtain 10.1 g of yellow solid (58%).

Aufarbeitung

  1. additionpoured
  2. filtrationThe orange precipitate was filtered
  3. washwashed with water
  4. customdried at 60° C. under reduced pressure for 1 hour
  5. customThe crude product was purified by silica gel chromatography (SP1, eluant: n-hexane/ethyl acetate 2:8)

Quellen und Nachweise

ORD-Eintrag
ord-4e457fb01b9a4e2facf6d9dcb4d89066
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524707B2

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