Synthetic method for 4-bromo-5-thiazolecarboxylic acid ethyl ester

A technology of ethyl thiazole carboxylate and a synthesis method, which is applied in the field of pharmaceutical intermediates, can solve the problems of not finding synthesis route data and the like, and achieves the effects of low cost of raw materials and high yield

Inactive Publication Date: 2019-10-18
苏州络森生物科技有限公司
View PDF1 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Ethyl 4-bromothiazole-5-carboxylate is a new type of pharmaceutical intermediate, and no relevant synthetic route information has been found in the professional database for this product

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Synthetic method for 4-bromo-5-thiazolecarboxylic acid ethyl ester
  • Synthetic method for 4-bromo-5-thiazolecarboxylic acid ethyl ester
  • Synthetic method for 4-bromo-5-thiazolecarboxylic acid ethyl ester

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0016] A kind of synthetic method of 4-bromo-5-thiazole carboxylic acid ethyl ester, comprises the steps:

[0017] ①Mix cuprous bromide, acetonitrile and isoamyl nitrite, heat to 60°C, add ethyl 4-aminothiazole-5-carboxylate in batches, and react for 30 minutes after the addition, and cool the reaction solution after the reaction of the raw materials is complete to room temperature.

[0018] In step ①, two-step reactions mainly take place, and the chemical reaction formula is expressed as:

[0019]

[0020] The reaction will eventually produce nitrogen gas that does not need to be handled.

[0021] 2. the reaction solution obtained by step 1. is added in hydrobromic acid, extracted with ethyl acetate, and gets the organic phase;

[0022] ③ The organic phase obtained in step ② was washed with water, dried over anhydrous sodium sulfate, and concentrated through a column to obtain ethyl 4-bromo-5-thiazolecarboxylate.

Embodiment

[0025] ①Add 10.6g of cuprous bromide into a 250ml three-necked flask, add 100ml of acetonitrile and 6.9g of isoamyl nitrite, heat to 60°C, add 28g of ethyl 4-aminothiazole-5-carboxylate in batches, and complete the reaction 30min, wait for the raw materials to react completely, and cool the reaction solution to room temperature;

[0026] ②Add 80ml of 20wt% hydrobromic acid to the reaction solution, extract 3 times with 300ml of ethyl acetate, and take the organic phase;

[0027] ③ Wash the organic phase with water, dry it with anhydrous sodium sulfate, and concentrate to obtain the crude product. Use 200-300 mesh silica gel as the stationary phase, petroleum ether / ethyl acetate (volume ratio 20:1, 15:1, 10:1, 5:1) was used as the eluent to wash the column successively to obtain 36 g of ethyl 4-bromo-5-thiazolecarboxylate, with a yield of 95%.

[0028] In step ①, ethyl 4-aminothiazole-5-carboxylate is added in batches to the reaction solution, and the latter batch is added aft...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

PropertyMeasurementUnit
densityaaaaaaaaaa
boiling pointaaaaaaaaaa
flash pointaaaaaaaaaa
Login to view more

Abstract

The invention belongs to the technical field of pharmaceutical intermediates, and relates to a synthetic method for 4-bromo-5-thiazolecarboxylic acid ethyl ester. The method comprises the following steps: mixing copper bromide, acetonitrile and isoamyl nitrite, performing heating to 60 DEG C, adding ethyl 4-aminothiazole-5-carboxylate in batches, after addition is completed, performing a reactionfor 30 min, after the raw materials are completely reacted, cooling the reaction solution to a room temperature, adding the cooled solution into hydrobromic acid, performing extraction by using ethylacetate, washing the organic phase by using water, performing drying by using anhydrous sodium sulfate, performing concentration, and performing treatment by using a chromatographic column to obtain the 4-bromo-5-thiazolecarboxylic acid ethyl ester. The method provided by the invention has low costs of the raw materials and a high yield, and is suitable for scale-up production.

Description

technical field [0001] The invention relates to the technical field of pharmaceutical intermediates, in particular to a method for synthesizing ethyl 4-bromo-5-thiazolecarboxylate. Background technique [0002] Monobrominated thiazole derivatives are often used as substructures for molecular structure modification of drug precursors due to their good reactivity, and ethyl 4-bromo-5-thiazolecarboxylate is one of them. 4-bromo-5-thiazolecarboxylic acid ethyl ester, English name is 4-bromo-5-thiazolecar boxylic acid ethyl ester, CAS number: 152300-59-9, molecular weight: 236.08634, density: 1.654g / cm 3 , the boiling point is 289°C at 760mmHg, and the flash point is 129°C. Its structural formula is as follows: [0003] [0004] Ethyl 4-bromothiazole-5-carboxylate is a new type of pharmaceutical intermediate. There is no relevant synthetic route information for this product in the professional database. [0005] Therefore, it is necessary to develop a new synthetic method t...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/56
CPCC07D277/56
Inventor 陆林林
Owner 苏州络森生物科技有限公司
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap