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Preparation method of 4-propythio-2-nitroaniline

A technology of nitroaniline and o-nitroaniline, which is applied in the field of preparation of 4-propylthio-2-nitroaniline, can solve the problems of affecting the economic benefits of industrial production, poor industrialization feasibility, complicated operation steps, etc. Low, easy to purify, simple production process

Active Publication Date: 2019-11-26
SHANDONG GUOBANG PHARMA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The weak point of above method: the one, in 2-nitro-4-thiocyanatoaniline synthetic process, produce impurity more, yield is relatively low; The 2nd, step 2 has introduced sodium cyanide as reaction raw material, cyanide Sodium is a highly poisonous substance. It is obvious that the above-mentioned highly toxic substance sodium cyanide is used, which is inconvenient to use and poor in safety, difficult in examination and approval, and poor in industrialization feasibility; the third is that in the propylation reaction process, the raw material is n-propane bromide, which is expensive and relatively expensive. high
The main shortcoming of above-mentioned two patent methods is to use a large amount of bromine, not only there is the problem of a large amount of waste of resources, for example, only about 1 ton of ammonium chloride, ammonium thiocyanate waste salt produced in the thiocyanation reaction Bendazole products have 1 ton of solid waste and 3 tons of waste water, and the output of three wastes in industrial production is large, which does not meet the needs of today's pursuit of green, energy-saving and environmental protection concepts
[0006] The preparation method of 2-nitro-4-thiocyanatoaniline disclosed in the above patent still needs to be further improved in the application of large-scale industrial production. In addition, there are problems of complicated operation steps and low product yield, which affect the overall industry. economics of production

Method used

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  • Preparation method of 4-propythio-2-nitroaniline

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Experimental program
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Effect test

Embodiment 1

[0027] The method for preparing 4-propylthio-2-nitroaniline, comprises the following steps:

[0028] (1) Condensation reaction: Add methanol 120g, o-nitroaniline 30g, disulfur dichloride 30.80g, acidified active clay / pseudoboehmite composite catalyst (mass ratio 1:1) 1.5 g is the catalyst. It was condensed at 25° C. for 3 hours to form bidisulfide. The catalyst was filtered for further use. 36.09 g of bidisulfide was obtained by separation, and the condensation reaction yield was 98.24%.

[0029] (2) Alkylation reaction: Add 36.09g of bidisulfide and 72.17g of methanol prepared in step (1) to a 250ml four-necked bottle, add 56.37g of sodium sulfide nonahydrate, keep warm for 30min, and control the temperature at 55 18.30 g of chloropropane was added dropwise at ℃ to generate 4-propylthio-2-nitroaniline, and 44.38 g of 4-propylthio-2-nitroaniline was obtained by isolation, and the yield of the alkylation reaction was 98.05%.

[0030] The total yield of 4-propylthio-2-nitroanil...

Embodiment 2

[0032] The method for preparing 4-propylthio-2-nitroaniline, comprises the following steps:

[0033] (1) Condensation reaction: Add methanol 120g, o-nitroaniline 30g, disulfur dichloride 29.33g, acidified active clay / pseudoboehmite composite catalyst (mass ratio 1:1) 1.5 g is the catalyst. It was condensed at 25° C. for 3 hours to form bidisulfide. The catalyst was filtered for further use. 33.43 g of bidisulfide was obtained by separation, and the condensation reaction yield was 91.01%.

[0034] (2) Alkylation reaction: Add 33.43g of bidisulfide and 66.86g of methanol prepared in step (1) into a 250ml four-necked bottle, add 52.23g of sodium sulfide nonahydrate, keep warm for 30min, and control the temperature at 55 16.96 g of chloropropane was added dropwise at ℃ to react to generate 4-propylthio-2-nitroaniline. 40.10 g of 4-propylthio-2-nitroaniline was isolated, and the yield of the alkylation reaction was 95.64%.

[0035] Preparation of 4-propylthio-2-nitroaniline react...

Embodiment 3

[0037] The method for preparing 4-propylthio-2-nitroaniline, comprises the following steps:

[0038] (1) Condensation reaction: Add methanol 120g, o-nitroaniline 30g, disulfur dichloride 30.80g, acidified activated clay / pseudoboehmite composite catalyst (mass ratio 1:1) 0.75 g is the catalyst, which is condensed at 25° C. for 3 hours to form bidisulfide. The catalyst is filtered for further use, and 28.15 g of bidisulfide is obtained by separation, with a condensation reaction yield of 76.64%.

[0039] (2) Alkylation reaction: Add 28.15 g of disulfide and 56.30 g of methanol prepared in step (1) to a 250 ml four-necked bottle, add 43.98 g of sodium sulfide nonahydrate, keep warm for 30 minutes, and control the temperature at 55 14.28 g of chloropropane was added dropwise at ℃ to react to generate 4-propylthio-2-nitroaniline. 34.44 g of 4-propylthio-2-nitroaniline was isolated, and the yield of the alkylation reaction was 97.55%.

[0040] The total yield of the reactions for ...

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Abstract

The invention discloses a preparation method of 4-propythio-2-nitroaniline, and solves the technical problems of unreasonable preparation method, high raw material price, high toxicity, complex operation, high cost, large production of three wastes, low yield and unsuitability for industrial production in the prior art. The preparation method of 4-propythio-2-nitroaniline provided by the inventiontakes o-nitroaniline, disulfur dichloride and chloropropane as the raw materials, and carries out condensation reaction and alkylation reaction in order under the action of a catalyst so as to obtain4-propythio-2-nitroaniline. The method can be widely applied technical field of synthesis of albendazole.

Description

technical field [0001] The invention belongs to the technical field of albendazole synthesis, in particular to a preparation method of 4-propylthio-2-nitroaniline. Background technique [0002] Albendazole was developed by Smith Kline Bichem Company (predecessor of GlaxoSmithKline). It is a broad-spectrum thiabendazole anthelmintic drug, which can be used for humans and animals, and can inhibit the growth of parasites. Growth and reproduction, by inhibiting the intestinal tract of worms or absorbing protein in cells, resulting in the inability of worms to take in sugar for survival, depleting the endogenous glycogen of worms, inhibiting the fumarate reductase system, and preventing the production of adenosine triphosphate , so that the worms cannot survive and reproduce, and eventually the worms gradually die due to energy exhaustion. Albendazole has the effect of completely killing hookworm eggs and whipworm eggs and partially killing roundworm eggs, and can also kill and ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C319/14C07C323/36
CPCC07C319/14C07C319/22C07C323/36C07C323/33
Inventor 王兴国李琦斌刘聪乔建超
Owner SHANDONG GUOBANG PHARMA
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