4-Chlorobenzonitrile → HCID 57750306、化合物

温度

-70 °C

A 2.5M solution of N-butyllithium (8.00 mL, 20.00 mmol) in hexanes, was added dropwise to 2-methylthiazole (1.983 g, 20 mmol) dissolved in THF (35.00 mL) over a period of 5 minutes under argon at −70° C. The resulting pale yellow slurry was stirred at −70° C. for 2.5 hour. 4-chlorobenzonitrile (2.75 g, 20.00 mmol) in THF (35.00 mL) was added dropwise to the suspension, which was stirred at −70° C. for 90 minutes after the end of the addition. The reaction mixture was allowed to warm to room temperature under stirring and darkened. The crude was concentrated to dryness and diluted with ethyl acetate then washed with water, dried over magnesium sulphate and concentrated. The crude product was purified by flash chromatography on silica gel eluting with 10 to 100% ethyl acetate in dichloromethane. The solvent was evaporated to dryness to afford (Z)-1-(4-chlorophenyl)-2-(thiazol-2-yl)ethenamine (1.466 g, 31.0%) as a pale yellow solid.

1. stirringwas stirred at −70° C. for 90 minutes
2. additionafter the end of the addition
3. temperatureto warm to room temperature
4. stirringunder stirring
5. concentrationThe crude was concentrated to dryness
6. additiondiluted with ethyl acetate
7. washthen washed with water
8. dry with materialdried over magnesium sulphate
9. concentrationconcentrated
10. customThe crude product was purified by flash chromatography on silica gel eluting with 10 to 100% ethyl acetate in dichloromethane
11. customThe solvent was evaporated to dryness

ORDレコード

ord-39b6bfe9ef8a414ea5978e6c0eb883e2

出典データセット

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08101623B2