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Preparation technology of 2-bromo-3,5,6-trichloropyrazine

A technology for the preparation of trichloropyrazine, which is applied in the field of preparation of 2-bromo-3,5,6-trichloropyrazine, can solve the problems of difficult product purification, low selectivity, and many by-products, and achieve easy Separation, high selectivity, low cost effect

Inactive Publication Date: 2018-03-30
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patented method involves reacting two chemicals called pyridazines with bromofluorene or another molecule that can be easily obtained from them at very small costs compared to traditional methods for producing these substances. These new ways make it easier than previous techniques such as synthesis but still have certain benefits over existing ones like those mentioned earlier.

Problems solved by technology

The technical problem addressed in this patented text rels specifically to improving the efficiency and purity of producing certain types of substances that can be useful or harmful when administered into humans through their use.

Method used

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  • Preparation technology of 2-bromo-3,5,6-trichloropyrazine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0011] A. Preparation of 2-amino-6-chloropyrazine

[0012] Add 2,6-dichloropyrazine (10.0 g, 67.1 mmol) and ammonia water (100 mL) into a hydrothermal reaction kettle, and react at 100° C. for 5 h. After the reaction was completed, it was cooled to room temperature, filtered with suction, and the filter cake was slurried with n-hexane (16 mL) to obtain 8.2 g of 2-amino-6-chloropyrazine as a white solid with a yield of 95.0%.

[0013] 1 H NMR (400 MHz, DMSO) δ: 7.70 (1H, d), 6.9 (2H, br s), 7.80 (1H, d). 13 C NMR (100 MHz, DMSO) δ 155.32, 141.92, 133.15, 131.15.

[0014] B. Preparation of 2-amino-3,5,6-trichloropyrazine

[0015] 2-Amino-6-chloropyrazine (2.0 g, 15.4 mmol) was dissolved in THF (50 mL), N-chlorosuccinimide (6.2 g, 46.3 mmol) was added, and the temperature was raised to reflux for 2 h. After the reaction was completed, cool to room temperature, pour the reaction solution into water, extract with ethyl acetate (40mL×3), collect the organic phase, dry over anhyd...

Embodiment 2

[0021] A. Preparation of 2-amino-6-chloropyrazine

[0022] 2,6-Dichloropyrazine (10.0 g, 67.1 mmol) and ammonia water (100 mL) were respectively added into a hydrothermal reaction kettle, and reacted at 60° C. for 18 h. After the reaction was completed, it was cooled to room temperature, filtered with suction, and the filter cake was slurried with n-hexane (16 mL) to obtain 6.3 g of 2-amino-6-chloropyrazine as a white solid with a yield of 72.5%.

[0023] 1 H NMR (400 MHz, DMSO) δ: 7.70 (1H, d), 6.9 (2H, br s), 7.80 (1H, d). 13 C NMR (100 MHz, DMSO) δ 155.32, 141.92, 133.15, 131.15.

[0024] B. Preparation of 2-amino-3,5,6-trichloropyrazine

[0025] 2-Amino-6-chloropyrazine (2.0 g, 15.4 mmol) was dissolved in THF (50 mL), N-chlorosuccinimide (4.1 g, 30.9 mmol) was added, and the temperature was raised to reflux for 3 h. After the reaction was completed, cool to room temperature, pour the reaction solution into water, extract with ethyl acetate (40mL×3), collect the organic...

Embodiment 3

[0030] A. Preparation of 2-amino-6-chloropyrazine

[0031] Add 2,6-dichloropyrazine (10.0 g, 67.1 mmol) and ammonia water (100 mL) into a hydrothermal reaction kettle, and react at 130° C. for 4 h. After the reaction was completed, it was cooled to room temperature, filtered with suction, and the filter cake was slurried with n-hexane (16 mL) to obtain 7.8 g of 2-amino-6-chloropyrazine as a white solid with a yield of 89.6%.

[0032] 1 H NMR (400 MHz, DMSO) δ: 7.70 (1H, d), 6.9 (2H, br s), 7.80 (1H, d). 13 C NMR (100 MHz, DMSO) δ 155.32, 141.92, 133.15, 131.15.

[0033] B. Preparation of 2-amino-3,5,6-trichloropyrazine

[0034] 2-Amino-6-chloropyrazine (2.0 g, 15.4 mmol) was dissolved in THF (50 mL), N-chlorosuccinimide (8.3 g, 61.8 mmol) was added, and the temperature was raised to reflux for 1 h. After the reaction was completed, cool to room temperature, pour the reaction solution into water, extract with ethyl acetate (40mL×3), collect the organic phase, dry over anhyd...

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Abstract

The invention discloses a preparation technology of 2-bromo-3,5,6-trichloropyrazine. The preparation technology comprises the following steps of using 2,6-dichloropyrazine as an initiating raw material, and performing ammoniation, halogenation and Sandmeyer reaction, so as to obtain a target compound, namely 2-bromo-3,5,6-trichloropyrazine. The preparation technology has the advantages that by adopting the synthesis route, the obtaining of raw materials is easy, the cost is low, the operation is simple, the product can be easily separated, the selectivity is high, the yield is higher, the total yield can reach 62.7%, and the preparation technology is favorable for actual application.

Description

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Claims

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Application Information

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Owner GUIZHOU UNIV
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