Ammonium Chloride → [1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-3-(2-thienyl)-1H-pyrazol-4-yl]acetonitrile

A solution of p-toluenesulfonylmethylisocyanide (0.95 g) in dimethoxyethane (10 ml) was added to a mixture of potassium tert-butoxide (1.01 g) and dimethoxyethane (10 ml) at −78° C., and the mixture was stirred for 5 minutes. A solution of 1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-3-(2-thienyl)-1H-pyrazole-4-carbaldehyde (2.01 g) in dimethoxyethane (20 ml) was added to the mixture, and then stirred at the same temperature for 1 hour, and at room temperature for 1 hour. Methanol (40 ml) was added to the mixture, and reflux was conducted for 1 hour. After cooling, the reaction mixture was poured into saturated aqueous ammonium chloride solution, and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), and concentrated. The residue was subjected to silica gel chromatography to obtain [1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-3-(2-thienyl)-1H-pyrazol-4-yl]acetonitrile (1.69 g, yield: 78%) as a colorless oily substance from the fraction eluted with ethyl acetate-hexane (1:3, volume ratio).

1. stirringstirred at the same temperature for 1 hour
2. waitat room temperature for 1 hour
3. temperaturereflux
4. waitwas conducted for 1 hour
5. temperatureAfter cooling
6. extractionextracted with ethyl acetate
7. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
8. dry with materialdried (MgSO4)
9. concentrationconcentrated

ORD record

ord-6bd7ee6e00b64136bec2f2346936d748

Source dataset

uspto-grants-2007_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07179823B1