Dimethylformamide → 5-Benzothiazolecarbonitrile

HRID 1507544Notizen

Reaktionsgleichung

Br[C:2]1[CH:3]=[CH:4][C:5]2[S:9][CH:8]=[N:7][C:6]=2[CH:10]=1.[CH3:11][N:12](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>[S:9]1[C:5]2[CH:4]=[CH:3][C:2]([C:11]#[N:12])=[CH:10][C:6]=2[N:7]=[CH:8]1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

Into a mixture of 5-bromo-1,3-benzothiazole (300 mg, 1.40 mmol, 1.00 equiv) and zinc cyanide (131.6 mg, 0.80 equiv) in N,N-dimethylformamide (6.0 mL) was added Pd(PPh3)4 (80.9 mg, 0.07 mmol, 0.05 equiv) and nitrogen was bubbled for 5 min. The resulting mixture was heated overnight at 80° C., quenched by water (15.0 mL), and extracted with ethyl acetate (3×15 mL). The combined organic layers were washed with brine (2×15 mL) and dried over Na2SO4. After filtered and concentrated under reduced pressure, the residue was purified by flash chromatography on silica gel, eluting with a mixture of 5-10% ethyl acetate in petroleum ether to afford the title compound as a light yellow solid. MS m/z [M+H]+ (ESI): 161.

Aufarbeitung

customwas bubbled for 5 min
customquenched by water (15.0 mL)
extractionextracted with ethyl acetate (3×15 mL)
washThe combined organic layers were washed with brine (2×15 mL)
dry with materialdried over Na2SO4
filtrationAfter filtered
concentrationconcentrated under reduced pressure
customthe residue was purified by flash chromatography on silica gel
washeluting with a mixture of 5-10% ethyl acetate in petroleum ether

Quellen und Nachweise

ORD-Eintrag: ord-4c90cfa129fe4e0b9538ebb17075bc13
Quelldatensatz: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09221809B2

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