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Synthesis method of 2-(2-methoxy-4-nitrophenyl)-3-(4-nitrophenyl)-5-(2,4-disulfophenyl)-2H-tetrazole monosodium salt

A technology of disulfobenzene and a synthesis method, applied in directions such as organic chemistry, can solve the problems of low total yield, high price, high toxicity, etc., and achieve the effects of easy post-processing, simple and safe operation

Inactive Publication Date: 2012-12-26
ZHENGZHOU UNIV
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Problems solved by technology

[0007] The above two methods respectively use n-butyl nitrite and chlorine as oxidants, which have the disadvantages of high price, high toxicity and low total yield.

Method used

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  • Synthesis method of 2-(2-methoxy-4-nitrophenyl)-3-(4-nitrophenyl)-5-(2,4-disulfophenyl)-2H-tetrazole monosodium salt
  • Synthesis method of 2-(2-methoxy-4-nitrophenyl)-3-(4-nitrophenyl)-5-(2,4-disulfophenyl)-2H-tetrazole monosodium salt
  • Synthesis method of 2-(2-methoxy-4-nitrophenyl)-3-(4-nitrophenyl)-5-(2,4-disulfophenyl)-2H-tetrazole monosodium salt

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Embodiment 1

[0027] 1. Compound 3 preparation of

[0028] take compound 2 ( 4.94g, 0.0322mol ) into a 500ml three-neck flask, add 150ml of methanol, heat and stir until reflux and dissolve. Cool to 50°C, slowly add compound 1 (10.0g, 0.0322mol). Keep the temperature at 50°C and continue to stir for 2h. Suction filtration under reduced pressure, washing with a small amount of methanol to obtain the compound 3 ( 11.065g, 0.0249mol ), yield 77.4%.

[0029] 1 H-NMR ( 400MHz, D 2 O) δ H : 6.83( d, 2H, J = 9Hz ), 7.65( dd, 1H, J = 8Hz, 1Hz), 7.81( d, 2H, J = 9Hz ), 7.93( d, 1H, J = 8Hz ), 8.03( d, 1H, J = 1Hz ), 8.31( s, 1H).

[0030] 2. Preparation of 4-nitro-2-methoxydiazonium salt

[0031] Take 2-methoxy-4-nitroaniline (3.7g, 0.0220mol) in a 50ml single-necked bottle, put it in an ice bath at -10~0°C, add 6.67ml of concentrated hydrochloric acid and 15ml of hydrochloric acid solution diluted with water. Stir for 5min. Then a solution obtained by dissolving (1.64g, 0.0237...

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Abstract

The invention discloses a synthesis method of 2-(2-methoxy-4-nitrophenyl)-3-(4-nitrophenyl)-5-(2,4-disulfophenyl)-2H-tetrazole monosodium salt (WST-8), belonging to the technical field of chemical synthesis. According to the synthesis method, the raw materials benzaldehyde-2,4-sodium disulfonate and p-nitrophenylhydrazine are subjected to four-step reaction by using N-bromosuccinimide (NBS) as an oxidizer, thereby obtaining the WST-8. The invention is safe and simple to operate and easy for after-treatment, and avoids using chlorine gas, n-butyl nitrite and other high-toxicity high-price compounds; and the total yield of the four-step reaction is up to 34.4%, thereby being beneficial to industrial production.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis and relates to a synthesis method of tetrazolium monosodium salt WST-8. Background technique [0002] WST-8, the chemical name is 2-(2-methoxy-4-nitrophenyl)-3-(4-nitrophenyl)-5-(2,4-disulfobenzene)-2H-tetrazole Monosodium salt is a main component in the cell viability detection reagent CCK-8 kit. The CCK-8 kit is a kit developed by the Dojindo Research Institute in Japan for the detection of cell proliferation and cytotoxicity. The kit is convenient to use, high in sensitivity, good in repeatability, and non-radioactive. However, the kit is expensive, and its main component, WST-8, is commercially available at a high price. The main synthetic methods of WST-8 reported at present are as follows: [0003] 1. Use benzaldehyde-2, 4-sodium disulfonate and p-nitrophenylhydrazine as raw materials to generate hydrazone; hydrazone is coupled with 2-methoxy-4-nitrodiazonium salt to obtain fo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D257/04
Inventor 刘宏民张恩何慧丽徐锦梅贺鹏郑甲信
Owner ZHENGZHOU UNIV
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