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Synthesizing method of isonicotinyl hydrazine azide

A technology of isonicotinyl azide and synthesis method, which is applied in the direction of organic chemistry and the like, can solve the problems of incapable of mass production, complicated operation, long cycle, etc., and achieves the reduction of synthesis cost, simple operation process, and simple and clear process route. Effect

Active Publication Date: 2012-06-20
NORTHWEST A & F UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] The present invention provides a method for synthesizing isonicotinoyl azide to overcome the problems in the prior art of complex operations, use of a large amount of organic solvents, long period, high cost and inability to be used in mass production

Method used

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  • Synthesizing method of isonicotinyl hydrazine azide

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Embodiment 1

[0026] A synthetic method of isonicotinoyl azide, comprising the steps in turn:

[0027] (1) In the reaction kettle, according to the ratio of isoniazid moles: HCl moles=1.0:2.5, add 0.1 moles of isoniazid and 35 milliliters of hydrochloric acid aqueous solution, stir at 0°C until dissolved, the mass of hydrochloric acid aqueous solution The percentage concentration is 26%.

[0028] (2) Add 6.9 grams of sodium nitrite aqueous solution dropwise according to the ratio of moles of isoniazid:moles of sodium nitrite=1.0:1.0 under stirring, and keep the reaction temperature at 0°C-5.0°C. After the dropwise addition, the temperature was still kept at 0°C to 5°C, and the reaction was stirred for another 2h.

[0029] (3) Slowly add an aqueous solution of sodium carbonate with a concentration of 10% by mass to the reaction system under stirring until pH=7, a large amount of white crystals are precipitated from the reaction solution, filtered, and dried with concentrated sulfuric acid t...

Embodiment 2

[0031] A synthetic method of isonicotinoyl azide, comprising the steps in turn:

[0032] (1) In the reactor, add 1 mole of isoniazid and 425 milliliters of hydrochloric acid aqueous solution according to the ratio of isoniazid moles: HCl moles=1.0:3.5, stir at 0°C until dissolved, the mass of hydrochloric acid aqueous solution The percentage concentration is 30%.

[0033] (2) Add dropwise the sodium nitrite aqueous solution of 103 grams according to isoniazid molar number: the ratio of sodium nitrite molar number=1.0:1.5 under stirring, and keep reaction temperature at 0 ℃~5.0 ℃, after dropwise addition, Still keeping the temperature at 0°C to 5°C, the reaction was stirred for another 1h.

[0034] (3) Slowly add an aqueous solution of sodium carbonate with a mass percentage concentration of 15% to the reaction system under stirring until pH = 7, a large amount of white crystals are precipitated from the reaction solution, filtered, and dried with concentrated sulfuric acid to...

Embodiment 3

[0036] A synthetic method of isonicotinoyl azide, comprising the steps in turn:

[0037] (1) In the reactor, add 1.5 moles of isoniazid and 586 milliliters of hydrochloric acid aqueous solution according to the ratio of moles of isoniazid: moles of HCl=1.0:3.0, and stir until dissolved at 0° C., the mass of aqueous hydrochloric acid The percentage concentration is 28%.

[0038](2) Add dropwise the sodium nitrite aqueous solution of 124 grams according to isoniazid molar number: the ratio of sodium nitrite molar number=1.0:1.2 under stirring, and keep reaction temperature at 0 ℃~2 ℃, after dropwise addition, Still keeping the temperature at 0°C to 2°C, the reaction was stirred for another 1.5h.

[0039] (3) Slowly add an aqueous solution of sodium carbonate with a mass percentage concentration of 17.2% to the reaction system under stirring until pH = 7, a large amount of white crystals are precipitated from the reaction solution, filtered, and dried with concentrated sulfuric ...

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Abstract

The invention relates to the technical field of chemical synthesis, in particular to a synthesizing method of isonicotinyl hydrazine azide. The method overcomes the problems of complicated operation, using a large amount of organic solvent, long cycle length, high cost and being not suitable for mass production of the prior art. The adopted technical scheme is as follows: the synthesizing method of isonicotinyl hydrazine azide comprises the following steps: (1) in a reaction kettle, adding water solution of isoniazide and hydrochloric acid and stirring to dissolve; (2) dropwise adding water solution of sodium nitrite under stirring and keeping the reaction temperature at 0 DEG C to 5.0 DEG C; and (3) adding water solution slowly in the reaction system under stirring, precipitating crystalfrom the reaction solution, filtering, drying and obtaining high-purity isonicotinyl hydrazine azide. Compared with the prior art, the method has the advantages of 1.high yield and stability; 2.simple preparing steps, 3.environment protection; and 4.being suitable for industrial production.

Description

Technical field: [0001] The invention relates to the technical field of chemical synthesis, in particular to a method for synthesizing isonicotinoyl azide. Background technique: [0002] Isonicotinoyl azide is the nitrosation product of isoniazid with the molecular formula C 6 N 4 h 4 O, the structural formula is [0003] [0004] The appearance is white amorphous crystal, the melting point is 45℃~50℃, relatively flammable and explosive. It is widely used as a raw material for the synthesis of highly active plant growth regulator 1-(4-pyridyl)-3-phenylurea. [0005] Isonicotinoyl azide was first synthesized by Carrana et al. in 1953 (G. Carrana, et al. Gazz. Chim. Ital. 83, 459). Its concrete synthetic method is, the isoniazid (4-H 2 NNHCOC 5 h 4 N) Dissolve in 33.6ml of 21.65% hydrochloric acid and stir at 0°C for 30min. Add 0.2mol of sodium nitrite aqueous solution 30ml dropwise between 0°C and 5°C. After completion, stir at 0°C for 30min. The reaction solution...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/78
Inventor 郭立尹明安
Owner NORTHWEST A & F UNIV
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