ChemicalBook CAS DataBase List 2-Chloro-5-methylthiazole

2-Chloro-5-methylthiazole synthesis

6synthesis methods

Product Name:2-Chloro-5-methylthiazole
CAS Number:33342-65-3
Molecular formula:C4H4ClNS
Molecular Weight:133.6

7305-71-7

33342-65-3

(1) Preparation of 2-chloro-5-methylthiazole: 72 g (0.6 mol) of tert-butyronitrile was dissolved in 1.5 L of anhydrous acetonitrile to prepare a solution. Under nitrogen protection, 65 g (0.48 mol) of anhydrous copper (II) chloride was added to the reaction vessel. Under vigorous stirring and nitrogen atmosphere, the tert-butyl nitrile solution was slowly added to the reaction vessel. Subsequently, 45.6 g (0.40 mol) of 2-amino-5-methylthiazole was added in batches at 25 °C for about 40 min addition. The reaction mixture was continued to be stirred at 25°C for 2 hours. Upon completion of the reaction, the reaction was quenched by the addition of 20% hydrochloric acid solution. The solvent was removed by distillation under reduced pressure. To the residue, 300 mL of chloroform was added and the organic phase was washed with saturated saline (100 mL x 3). The organic layer was dried with anhydrous magnesium sulfate and the solvent was removed by distillation under reduced pressure to give 49.7 g of 2-chloro-5-methylthiazole in 93% yield.

7305-71-7 Synthesis

7305-71-7
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$6.00/10g

33342-65-3
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Yield: 93%

Reaction Conditions:

with t-butyl thionitrite;copper dichloride in acetonitrile at 25; for 2.66667 h;Inert atmosphere;

Steps:

1.1 (1) Preparation of 2-chloro-5-methylthiazole:
72 g (0.6 mol) of t-butyl sulfonitrile was dissolved in dry acetonitrile (1.5 L) to prepare a solution.The reactor was purged with nitrogen, then 65 g (0.48 mol) of dry anhydrous copper (II) chloride was added, and the prepared t-butyl sulfonitrile solution was added to the reaction vessel under vigorous stirring and nitrogen protection, and then kept. 2-Amino-5-methylthiazole (45.6 g, 0.40 mol) was added portionwise over a period of 40 min at 25 °C.The reaction mixture was reacted at 25 ° C for 2 h.Then 20% hydrochloric acid solution was added.The solvent was distilled off under reduced pressure, and then 300 ml of chloroform was added thereto, and 100 mL × 3 was washed with brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give 49.7 g of 2-chloro-5-methylthiazole, yield 93%;

References:

Zhejiang Yongtai Technology Co., Ltd.;Shao Hongming;Lin Jiaohua;Chen Shaoting;Li Yijun CN108164522, 2018, A Location in patent:Paragraph 0027; 0028; 0032; 0036

6593-86-8 Synthesis