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ChemicalBook CAS DataBase List 2-CHLOROTHIAZOLE-5-CARBONITRILE

2-CHLOROTHIAZOLE-5-CARBONITRILE synthesis

3synthesis methods
-

Yield:51640-36-9 67%

Reaction Conditions:

with copper dichloride;isopentyl nitrite in acetonitrile; for 10.5 h;

Steps:

45.1

3.4 g (27 mmol) 2-Amino-5-cyanothiazole (Example 43) and 5.1 g (30 mmol) dihydrated cupric chloride were dispersed in 100 ml acetonitrile. To the mixture, with vigorous stirring, 5.7 ml solution of isoamyl nitrite in acetonitrile was added rapidly dropwise over 30 min, followed by continuing the reaction for 10 hr. The reaction mixture was concentrated, dissolved in ethyl acetate, and filtered to remove insoluble matters. The organic phase was concentrated, and separated by a column chromatography to obtain 2.6 g of a liquid (yield 67%), which was placed aside to precipitate a needle crystal with mp 54-57°C, 13C NMR (CDCl3,ppm) 108.16, 110.41, 150.59, 157.36; MS(EI)144.1(M+).

References:

EP2039686,2009,A1 Location in patent:Page/Page column 32-33