3-Hydroxybenzaldehyde → N-{3-[2-(4-hydroxyphenyl)vinyl]-1,3-thiazol-2-yl}acetamide

Temperature

0 °C

To a solution of {[2-(acetylamino)-1,3-thiazol-4-yl]methyl}(triphenyl)phosphonium chloride (3.894 g, 8.598 mmol) and 3-hydroxybenzaldehyde (1.000 g, 8.189 mmol) in anhydrous N,N-dimethylformamide (42 ml) was added dropwise potassium tert-butoxide tetrahydrofuran solution (1M, 25.4 ml, 25.4 mmol) at 0° C. After stirring at 0° C. for 30 min, the mixture was stirred at room temperature for 2 hr. The reaction mixture was cooled to 0° C., and iced water (100 ml) was added. The mixture was washed twice with ethyl acetate, and the aqueous layer was acidified with 1M hydrochloric acid (pH 2.5). The mixture was extracted 3 times with ethyl acetate, and the combined organic layer was washed twice with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. BW-300SP 120 g, ethyl acetate:hexane=1:1) to give N-{3-[2-(4-hydroxyphenyl)vinyl]-1,3-thiazol-2-yl}acetamide (1.953 g, 7.503 mmol, yield 91.6%) as a slightly yellow solid.

1. stirringthe mixture was stirred at room temperature for 2 hr
2. temperatureThe reaction mixture was cooled to 0° C.
3. washThe mixture was washed twice with ethyl acetate
4. extractionThe mixture was extracted 3 times with ethyl acetate
5. washthe combined organic layer was washed twice with saturated brine
6. dry with materialdried over anhydrous magnesium sulfate
7. concentrationconcentrated under reduced pressure
8. customThe residue was purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. BW-300SP 120 g, ethyl acetate:hexane=1:1)

ORD record

ord-9116285542284810872c853db6a962a4

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08507690B2