Chlorosuccinimide → 5-Chloro-4-(trifluoromethyl)-1,3-thiazol-2-amine

2-Amino-4-trifluoromethylthiazole (10 g) was dissolved in acetonitrile (80 ml) and N-chlorosuccinimide (8.8 g) was added at room temperature with stirring. The mixture was refluxed for 9 hr and the solvent was removed under reduced pressure. The residue was dissolved in chloroform and washed with cold diluted aqueous sodium hydroxide. The chloroform layer was dried over magnesium sulfate and the solvent was removed under reduced pressure to give crude 2-Amino-5-chloro-4-trifuloromethylthiazole (12 g). It was recrystallized from n-hexane-benzene (1:1 mixture) as colorless needles (6.8 g), m. p. 107-108° C.

1. temperatureThe mixture was refluxed for 9 hr
2. customthe solvent was removed under reduced pressure
3. dissolutionThe residue was dissolved in chloroform
4. washwashed with cold diluted aqueous sodium hydroxide
5. dry with materialThe chloroform layer was dried over magnesium sulfate
6. customthe solvent was removed under reduced pressure
7. customto give crude 2-Amino-5-chloro-4-trifuloromethylthiazole (12 g)
8. customIt was recrystallized from n-hexane-benzene (1:1 mixture) as colorless needles (6.8 g), m. p. 107-108° C.

ORD record

ord-c3b9ecd81ef7451fa14d1e14a46d0936

Source dataset

uspto-grants-2004_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06737382B1