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Preparation method of 4-thiophenyl-o-phenylenediamine

A technology of phenylthioaniline and o-phenylenediamine, which is applied in the field of preparation of 4-phenylthioaniline-o-phenylenediamine, and can solve problems such as complicated operation, high cost, and difficult treatment of three wastes

Inactive Publication Date: 2021-07-30
SHANDONG GUOBANG PHARMA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method has low efficiency in the reaction process of 2-nitro-4-thiocyanatoaniline and bromide. If benzyl bromide is replaced by bromobenzene, the activity will be lower, and the treatment of three wastes is relatively difficult, so it is not suitable for industrial production. , it is necessary to find a compound that can replace bromobenzene for the reaction
[0007] The above-mentioned preparation method is not suitable for large-scale application and production, and has problems such as complicated operation, high cost, and poor safety and sanitation conditions, which affect economic benefits and need further improvement

Method used

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  • Preparation method of 4-thiophenyl-o-phenylenediamine
  • Preparation method of 4-thiophenyl-o-phenylenediamine
  • Preparation method of 4-thiophenyl-o-phenylenediamine

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Experimental program
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Effect test

Embodiment 1

[0020] (1) Hydrolysis reaction: 2-nitro-4-thiocyanine is added 39.00 g (0.20 mol), 100 g of purified water, add 48.04 g (0.20 mol), 40-50, 48.04 g (0.20 mol), 40-50, 48.04 g (0.20 mol), 40-50 The incubation was 60 min, and the hydrolysis was 34.65 g sodium 3-nitro-4-aminephenyl thionyl sulfur, yield was 90.24%. The reaction equation is as follows:

[0021]

[0022] (2) Heavy nitriding reaction: 50 g of purified water was added to 250 ml of four o'cloths, and 18.61 g (0.20 mol) of aniline was added thereto, and the concentrated hydrochloric acid was 60.83 g (content of 36%, 0.60 mol), and then ammonium nitrid 15.18 was added. G (0.22 mol) was dissolved in 30 g of purified water. Added to the four flasks, 8 ° C was injected for 30 min, and the reaction was generated from 27.772 g of nitride icy, yield 98.99%. The reaction equation is as follows:

[0023]

[0024] (3) Condensation Reaction: 32.64 g (0.17 mol) of 3- Nitro-4-aminephenylthiophenol sulfur sodium, 100 ml of purified w...

Embodiment 2

[0029] In this first embodiment, the second embodiment is different from the equivalent of sodium sulfide in the hydrolysis reaction, 2-nitro-4-thiocyanine 39.00 g (0.20 mol), 100g purified water, add Jiuwater in a 500 ml four-mouth bottle. Sodium sulfide was 52.84 g (0.22 mol), 40-50 ° C for 60 min, and 36.52 g of 36.52 g sodium 3-nitro-4-amine-based benzphenol was obtained, 95.11% yield.

Embodiment 3

[0031] In this first embodiment, the second embodiment is different from the equivalent of sodium sulfide in the hydrolysis reaction, 2-nitro-4-thiocyanine 39.00 g (0.20 mol), 100g purified water, add Jiuwater in a 500 ml four-mouth bottle. Sodium sulfide was 62.45 g (0.26 mol), 40-50 ° C for 60 min, and 36.87 g of 36.87 g of sodium thiosquiol sulfur sulfonol was obtained, and yield was 96.03%.

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Abstract

The invention provides a preparation method of 4-thiophenyl-o-phenylenediamine, wherein the preparation method comprises the steps: by taking 2-nitro-4-thiocyano aniline and aniline as initial raw materials, firstly, reacting 2-nitro-4-thiocyano aniline with sodium sulfide to obtain 3-nitro-4-amino thiophenol sodium, and reacting aniline with sodium nitrite under an acidic condition to generate benzene diazonium chloride; and then condensing the benzene diazonium chloride and the 3-nitro-4-amino thiophenol sodium to obtain 2-nitro-4-thiophenyl aniline, and then carrying out a Raney nickel hydrogenation reduction reaction to obtain the 4-thiophenyl-o-phenylenediamine. The method has the characteristics of high economic benefit, low three-waste amount, low cost and the like, the total yield can reach 64.58%, and the method belongs to the technical field of organic chemical industry.

Description

Technical field [0001] The present invention belongs to the art of organic chemical technology, and is related to the preparation of 4-phenylthio-physicine. Background technique [0002] 4-phenylthio-physicine is an important chemical raw material for a fentobenazole intermediate, a phenamazole is a benzimidazole drug, which is a low toxic, efficient, broad-spectral drive. Insect drugs, in addition to parasites such as hookworms, dewings, whipworms, some aphids and round nematoes, but also have a strong insectica, and have a long-term, safe and low-conditioning, and good quality. Etc. [0003] Currently, the preparation method of grains-Damazole is usually used: [0004] Article J. SmeterocyClic Chem., 41, 273 (2004). A method of preparation of flavonazole is disclosed. Based on 5-chloro-2-nitropheniline and benzene and benzene thiodethylideine by 5-chloro-2-nitrophenylideine, 2-nitro-5-phenylthio-amine is then prepared by catalyzed hydrogenation by palladium carbon. Amine, such ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C319/02C07C323/34C07C245/20C07C319/14C07C319/20C07C323/37
CPCC07C245/20C07C319/02C07C319/14C07C319/20C07C323/34C07C323/37
Inventor 邱正洲王召平肖兵王金辉周洪亮
Owner SHANDONG GUOBANG PHARMA
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