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Synthetic method of 2,2'-hydrazine-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt

A technology of benzothiazoline and hydroxybenzothiazole, applied in the field of chemical synthesis, can solve the problems of high price of ABTS and limited synthesis route, and achieve the effects of low cost, high yield and excellent synthesis route

Active Publication Date: 2021-12-03
上海瀚鸿科技股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the price of ABTS is relatively expensive, and the synthetic route is limited. It is still of great significance to seek a new optimized synthetic method for ABTS, which is also the meaning of the chemical substance methodology itself.

Method used

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  • Synthetic method of 2,2'-hydrazine-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt
  • Synthetic method of 2,2'-hydrazine-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] (1) Dissolve 2-hydroxybenzothiazole (1mol, 151g), 2-bromoethane (1.1mol, 120g) and potassium hydroxide (1mol, 56g) in 2L of tetrahydrofuran, stir at 0°C React for 1 hour, then react at room temperature for 2 hours, after the reaction is complete, spin off the tetrahydrofuran solvent, add 2L of ethyl acetate, wash twice with water, dry over anhydrous sodium sulfate, then spin off the ethyl acetate, wash with methyl tert-butyl ether Crystallization gave 150 g of 3-ethylbenzothiazol-2-one, with a yield of 84%. HNMR (DMSO- d 6 ,400MHz): 7.67-7.60 (m, 1H), 7.41-7.27 (m, 2H), 7.23-7.14 (m, 1H), 3.97(q, 2H), 1.19(t,3H).

[0024] (2) Dissolve 3-ethylbenzothiazol-2-one (1mol, 179g) obtained in step (1) in 1000mL of ethanol, add 80% hydrazine hydrate (0.625mol, 31g), heat and reflux for 4 hours , TLC detection, no reaction. Then add concentrated hydrochloric acid (0.12mol, 10mL), continue to stir, gradually precipitate, continue to react for 3 hours, cool, filter with suction...

Embodiment 2

[0029] (1) Dissolve 2-hydroxybenzothiazole (1mol, 151g), 2-bromoethane (1.2mol, 131g) and sodium hydroxide (1.1mol, 44g) in 2L of acetonitrile, at 0°C , stirred and reacted for 1 hour, then reacted at room temperature for 2 hours, after the reaction was completed, the acetonitrile solvent was spun off, 2L of dichloromethane was added, washed twice with water, dried over anhydrous sodium sulfate, then the dichloromethane was spun off, and methyl tert-butyl 153 grams of 3-ethylbenzothiazol-2-one were obtained by crystallization of the base ether, and the yield was 85%.

[0030] (2) Dissolve 3-ethylbenzothiazol-2-one (1mol, 179g) obtained in step (1) in 1000mL of methanol, add 80% hydrazine hydrate (0.625mol, 31g), and then add concentrated hydrochloric acid (0.14mol, 12mL), heated and refluxed for 4 hours, the reaction was completed, cooled, suction filtered and washed with cold methanol to obtain 151 grams of 2,2'-azinobis(3-ethylbenzothiazoline), yield 85 %.

[0031] (3) Slo...

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Abstract

The invention provides a synthesis method of 2,2'-hydrazine-bis(3-ethylbenzothiazoline-6-sulfonic acid) diamine salt (ABTS), which belongs to the field of organic synthesis. 2-Hydroxybenzothiazole first reacts with 2-bromoethane to generate 3-ethylbenzothiazol-2-one, and then reacts with hydrazine hydrate to generate 2,2'-azinobis(3-ethylbenzothiazoline ), and then react with concentrated sulfuric acid to generate compound 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid), and finally react with ammonia to form a salt to obtain 2,2'-bis(3-ethylbenzothiazoline-6-sulfonic acid) Ammonia-bis(3-ethylbenzothiazoline-6-sulfonic acid) diamine salt. The raw materials used in the invention are cheap and easy to obtain, the operation is simple and convenient, the reaction conditions are mild, and the yield is high.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a synthesis method of 2,2'-hydrazine-bis(3-ethylbenzothiazoline-6-sulfonic acid) diamine salt (ABTS). [0002] technical background [0003] 2,2'-hydrazine-bis(3-ethylbenzothiazoline-6-sulfonic acid) diamine salt (ABTS) can be used in biochemical research, spectroscopic reagent for free chlorine, color development of enzyme-linked immunosorbent assay Substrate, the substrate of peroxidase, used in ELISA experiment. Total Antioxidant Capacity Assay Kit (ABTS method), that is, Total Antioxidant Capacity Assay Kit with ABTSmethod, referred to as T-AOC Assay Kit, is a kind of using ABTS as a chromogen, which can be used for plasma, serum, saliva, urine, etc. A kit for detecting the total antioxidant capacity of various body fluids, cell or tissue lysates, plant or Chinese herbal medicine extracts, or various antioxidant solutions. At present, there are few reports on the ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D277/82
CPCC07D277/82
Inventor 余书强
Owner 上海瀚鸿科技股份有限公司
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