ETHYL 2-CHLOROTHIAZOLE-5-CARBOXYLATE synthesis
- Product Name:ETHYL 2-CHLOROTHIAZOLE-5-CARBOXYLATE
- CAS Number:81449-93-6
- Molecular formula:C6H6ClNO2S
- Molecular Weight:191.64
32955-21-8
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81449-93-6
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Yield: 40%
Reaction Conditions:
with tert.-butylnitrite;copper dichloride in tetrahydrofuran;acetonitrile at 23 - 65;
Steps:
3 Example 3: The synthesis of compound (2)
[0097] At 23°C, a solution of ethyl 2-aminothiazole-4-formate (1.0 g, 6.35 mmol) in acetonitrile (10 mL) and tetrahydrofuran(10 mL) is added to a solution (10 mL) of t-butyl nitrite (1.3 mL, 9.52 mmol) and cuprous chloride (1.0 g, 7.6mmol) in acetonitrile (10 mL) and tetrahydrofuran (10 mL). The reaction mixture is required to be heated at 65 °C untilcomplete consumption of the starting materials as shown by thin-layer chromatography (40% ethyl acetate-hexane).Then, the mixture is cooled to room temperature and partitioned between water and ethyl acetate. The organic layer isconcentrated under vacuum and purified by flash silica gel column chromatography eluted with 20% ethyl acetate-hexaneto give ethyl 2-chloro-thiazole-4-formate (compound (2-2)) (0.49 g, 40%).
References:
Hangzhou Bensheng Pharmaceutical Co., Ltd.;XU, Rongzhen;XIE, Fuwen;LAI, Hongxi;RONG, Frank EP2615092, 2013, A1 Location in patent:Paragraph 0095; 0097
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