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Preparation method of oxibendazole

A technology of propoxyimidazole and n-propanol, which is applied in the field of chemistry or medicine, can solve the problems of human injury, high price of acetaminophen, and great environmental hazards, and achieve the effect of small environmental and personal hazards

Inactive Publication Date: 2014-02-26
CHANGZHOU YABANG QH PHARMACHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The above method has the following disadvantages: (1) The price of raw material paracetamol is high, and the route cost is high; (2) The raw material used in condensation is bromopropane, and bromine-containing waste water is harmful to the environment, and the post-treatment is complicated; (3) Reduction Adopt tin protochloride or alkali sulfide, pollute greatly; (4) have adopted sulfur-containing cyclizing agent, and by-product is methyl mercaptan, and deodorant all causes pollution to atmosphere and water body, also can have anesthesia effect to bodily harm

Method used

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  • Preparation method of oxibendazole
  • Preparation method of oxibendazole
  • Preparation method of oxibendazole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Step 12, the preparation of 4-dichloronitrobenzene

[0036] In a 500ml four-necked flask, add 100.0g (0.68mol) of m-dichlorobenzene, 90.0g (0.90mol) of concentrated sulfuric acid, and 48.1g (0.75mol) of nitric acid, and keep the reaction at 5-10°C for 3 hours, then remove the waste from the lower layer. The acid layer was washed by adding 100 g of 5% aqueous sodium hydroxide solution, stirred and washed twice with 100 ml of water, and the lower layer was separated to obtain 125.0 (0.65 mol) g of 2,4-dichloronitrobenzene, which was directly used in the next reaction. This step yield is 95.7%, and content is 98.7%.

[0037] Step 22 - Preparation of nitro-5-chloroaniline

[0038] Add 100.0g (0.52mol) of 2,4-dichloronitrobenzene obtained in the previous step, 350g methanol, and 88.4g (5.2mol) of liquid ammonia to a 1000ml autoclave. The temperature is controlled at 130-140°C and the reaction pressure is 2.5 ~3.0MPa, react for 12 hours, cool down, release ammonia, slowly a...

Embodiment 2

[0047] Step 1 The preparation of 2,4-dichloronitrobenzene, the specific operation steps are the same as in Example 1, and the data are shown in Table 1;

[0048] Step 2 The preparation of 2-nitro-5-chloroaniline, the specific operation steps are the same as in Example 1, and the data are shown in Table 1;

[0049] Step 3 Preparation of 2-nitro-5-propoxyaniline

[0050] Add 80.0 g of n-propanol, 26.0 g (0.15 mol) of 2-nitro-5-chloroaniline and 14.8 g (0.18 mol) of sodium n-propoxide into a 500 ml four-necked flask. Heat up to 97°C and reflux for 5 hours, cool down to 60°C, slowly add 240ml of water, continue to cool down to 25°C and keep stirring for 3 hours. Filter, wash with water until neutral, and dry to obtain 25.1 g of 2-nitro-5-propoxyaniline. The yield is 85.2%, and the content is 97.5%.

[0051] Step 4 4-propoxy-1,2-phenylenediamine

[0052] In a 500ml four-necked flask with a thermometer and a stirring device, add isopropanol and 23.5g of 2-nitro-5-propoxyaniline ...

Embodiment 3

[0056] Step 1 The preparation of 2,4-dichloronitrobenzene, the specific operation steps are the same as in Example 1, and the data are shown in Table 1;

[0057] Step 2 The preparation of 2-nitro-5-chloroaniline, the specific operation steps are the same as in Example 1, and the data are shown in Table 2;

[0058] Step 3 The preparation of 2-nitro-5-propoxyaniline, the specific operation is the same as in Example 1, and the data are shown in Table 3;

[0059] Step 4 The preparation of 4-propoxy-1,2-phenylenediamine, the specific operation is the same as in Example 1, and the data are shown in Table 4;

[0060] Step 5 The preparation of propoxyimidazole, the specific operation is the same as in Example 1, and the data are shown in Table 5;

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Abstract

The invention relates to the field of chemistry or medicine, particularly a preparation method of oxibendazole. The invention provides a brand-new oxibendazole synthesis route: m-dichlorobenzene used as an initial raw material is subjected to nitration, ammonification, condensation, reduction and cyclization reaction to obtain the oxibendazole. The initial raw material acetaminophen in the existing industrial route is changed into the cheap m-dichlorobenzene; the condensation adopts alkali metal salt of npropanol or npropanol, and avoids using bromopropane to generate bromine-containing wastewater, thereby being environment-friendly; and the reduction technique uses a clean efficient reduction technique instead of sodium sulfide. The new synthesis technique is simple and efficient, has the advantages of low pollution and high quality, and is suitable for industrial production.

Description

technical field [0001] The invention relates to the field of chemistry or medicine, in particular to a preparation method of propoxyimidazole. Background technique [0002] Oxibendazole, also known as Oxibendazole and Oxibendazole, is a broad-spectrum benzimidazole anthelmintic drug. It was first successfully developed by SmithKline Pharmaceuticals of the United States and marketed as a veterinary drug. It is effective for horses and sheep. , dog, cat. Natural and secondary infection of nematodes, roundworms, hookworms, filarials, sporozoites and tapeworms in rats and mice have significant insecticidal effects. The insecticidal mechanism of propoxyimidazole is to inhibit the use of glycogen by parasites, resulting in the depletion of glycogen, so that parasites cannot survive and develop. Recently, reports have introduced the application of propoxyimidazole in anti-angiogenic drugs, anti-tumor drugs and anti-moist age-related macular degeneration drugs, as well as the appl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D235/32
CPCC07D235/32
Inventor 苏文杰朱建民吴建才王四香王学成
Owner CHANGZHOU YABANG QH PHARMACHEM
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