Ethylamine → N-((2-Chlorothiazol-5-yl)methyl)ethanamine

A 60˜70% aqueous solution of ethylamine (3.6 mL) and a 20% aqueous NaOH solution (8.0 mL) were added dropwise respectively into a solution of 2-chloro-5-chloromethylthiazole (3.40 g) in chloroform (40 mL), then benzyl triethyl ammonium chloride (0.1 g) was added. After stirring overnight at room temperature, the pH of the resulting mixture was adjusted to weak alkaline. The organic layer was separated while the aqueous layer was extracted with dichloromethane twice. The organic phases were combined, and dried over anhydrous sodium sulfate after washed with an iced aqueous sodium chloride solution twice, then remove the solvent under reduced pressure to obtain 2-chloro-5-ethylaminomethylthiazole 3.37 g as an oil in 95.2% purity. GC-MS: (M+) (EI, 70 eV, m/z) calc: 176. found: 176.

1. customThe organic layer was separated while the aqueous layer
2. extractionwas extracted with dichloromethane twice
3. dry with materialdried over anhydrous sodium sulfate
4. washafter washed with an iced aqueous sodium chloride solution twice
5. customremove the solvent under reduced pressure

ORD record

ord-c9d488a28e0f477f8546e96f6b97a188

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09386769B2