Potassium Carbonate → HCID 16413754, compound

MeOH (28 mL) was added to a round bottom flask containing K2CO3 (4.22 gm, 30.50 mmol), 1-(isocyanomethylsulfonyl)-4-methylbenzene (3.28 gm, 16.78 mmol), and 3-formylbenzonitrile (2.00 gm, 15.25 mmol). The reaction mixture was refluxed for 2 h. After this time, the mixture was concentrated under reduced pressure. The remaining residue was dissolved in water (50 ml). The aqueous solution was extract with EtOAc (50 ml). The EtOAc layer was washed with saturated aqueous NaCl (30 ml), dried over MgSO4, filtered and concentrated. The resulting residue was purified using silica gel chromatography eluting with a gradient of 0-100% EtOAc/Hexanes to give the product, 3-(oxazol-5-yl)benzonitrile, (1.05 gm, 6.17 mmol, 41% yield) as a yellow solid. Anal. Calcd. for C10H6N2O m/z 170.1, found: 171.0 (M+H)+.

1. temperatureThe reaction mixture was refluxed for 2 h
2. concentrationAfter this time, the mixture was concentrated under reduced pressure
3. dissolutionThe remaining residue was dissolved in water (50 ml)
4. extractionThe aqueous solution was extract with EtOAc (50 ml)
5. washThe EtOAc layer was washed with saturated aqueous NaCl (30 ml)
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated
9. customThe resulting residue was purified
10. washeluting with a gradient of 0-100% EtOAc/Hexanes

ORD record

ord-41d9d6b56b3043c4802fc0505c05c0ef

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08815909B2