Synthesis method for 3-amino-1,2,4-phentriazine-1,4-dioxide

A technology of benzotriazine and dioxide, which is applied in the field of synthesis of 3-amino-1,2,4-benzotriazine-1,4-dioxide, can solve the problem of harsh reaction conditions, high toxicity, Unstable yield and other problems, to achieve the effect of mild reaction conditions, simple operation and high safety

Inactive Publication Date: 2013-10-30
由国峰
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  • Abstract
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Problems solved by technology

[0003] The synthesis of existing 3-amino-1,2,4-benzotriazine-1,4-dioxide all adopts cyanamide solid as raw material, and cyanamide solid is

Method used

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  • Synthesis method for 3-amino-1,2,4-phentriazine-1,4-dioxide

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Embodiment

[0017] 1) Weigh 15g of o-nitroaniline and stir and raise it to 50°C, slowly add 18mL of 55% cyanamide solution dropwise, after the dropwise addition, heat up to 100°C, continue heating until the solution turns dark red; down to room temperature, orange Yellow solid precipitated out, add 12mol / L concentrated HCl 60mL dropwise, drip in 20 minutes; heat up again to 100℃, stir for 20-40 minutes, then cool to room temperature; add 16mol / L NaOH solution 60mL; After reacting for 15 hours at 100°C, a viscous solid was suspended. Stir slowly; add 100-200 mL of water, stir, and cool to room temperature. A yellow solid precipitated, filtered, washed with water, washed with ethyl acetate, and dried to obtain a pale yellow powder. -Amino-1,2,4-benzotriazine-1-oxide.

[0018] In this step, the reaction time is sufficient, the concentration of the cyanamide solution is moderate, and 19.7 g of 3-amino-1,2,4-benzotriazine-1-oxide can be obtained, and the yield is 90%.

[0019] 2) Weigh 5g of 3-ami...

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Abstract

The invention relates to a synthesis method for 3-amino-1,2,4-phentriazine-1,4-dioxide. The invention provides a synthesis method for 3-amino-1,2,4-phentriazine-1,4-dioxide, which is low in toxicity, moderate in reaction conditions, simple to operate, high in safety, and stable in yield. The method disclosed by the invention comprises the following steps of: firstly, co-heating ortho-nitroaniline in 55% cyanamide aqueous solution and concentrated HCl, cooling, then adding NaOH solution, and finishing a ring-closure reaction to generate an intermediate product, namely, 3-amino-1,2,4-phentriazine-1-oxide; secondly, adding the intermediate product, namely, 3-amino-1,2,4-phentriazine-1-oxide in CH3COOH to form a suspended matter, then adding H2O2 solution, and reacting in the dark to obtain 3-amino-1,2,4-phentriazine-1,4-dioxide solution; and finally, performing rotary evaporation on the obtained 3-amino-1,2,4-phentriazine-1,4-dioxide solution to remove a solvent, separating out a red solid substance, filtering, and recrystallizing a filter cake by absolute ethyl alcohol to obtain a 3-amino-1,2,4-phentriazine-1,4-dioxide crystal.

Description

Technical field [0001] The invention relates to an improvement in the synthesis method of tirapazamine. Background technique [0002] 3-Amino-1,2,4-benzotriazine-1,4-dioxide, also known as SR4233, molecular formula is C 7 H 6 N 2 O 2 , Molecular weight is 178.15, dark red powder, melting point 229℃, soluble in methanol, unstable in alkaline solution. It can damage DNA by breaking down into free radicals in hypoxic cells and produce cytotoxic effects. It is currently used in combination with cisplatin for stage III clinical head and neck tumors, and combined with cisplatin / etoposide for limited-stage small cell lung cancer And combined cyclophosphamide for phase I and II clinical studies of difficult-to-control solid tumors in children. [0003] The existing 3-amino-1,2,4-benzotriazine-1,4-dioxide synthesis uses solid cyanamide as a raw material, and the solid cyanamide is very unstable, resulting in the yield It is unstable and highly toxic; the reaction conditions are also harsh...

Claims

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Application Information

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IPC IPC(8): C07D253/10
Inventor 由国峰伍建辉
Owner 由国峰
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