A kind of synthetic method of 3,4-diamino-benzophenone

A technology of benzophenone and synthesis method, which is applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems of qualified product purity, low yield, and deconstruction, and achieves improved product purity and improved The effect of reaction yield

Active Publication Date: 2021-06-08
SUZHOU KAIYUAN MINSHENG SCI & TECH CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Method 1 and method 2 adopt ammonia water to carry out high-pressure reaction, and the 3-nitro-4-amino-benzophenone that obtains is not high in purity, and impurity is big, and yield is low
The products obtained by both methods contain impurities: 3-amino-4-hydroxy-benzophenone and 3-amino-4-chloro-benzophenone, which are difficult to handle in subsequent steps, with There are two bad consequences: the product purity is unqualified, the impurity content is removed from the label, or the product purity is qualified, and the yield drops significantly

Method used

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  • A kind of synthetic method of 3,4-diamino-benzophenone
  • A kind of synthetic method of 3,4-diamino-benzophenone
  • A kind of synthetic method of 3,4-diamino-benzophenone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] 1), put 3-nitro-4-chloro-benzophenone: 180g, ethanol: 200g and 15% (mass fraction) ammonia water: 300g into the autoclave, stir and heat up to 120-125°C, keep warm for 24h, At the same time, the pressure in the kettle reaches 0.55-0.60MPa. After the reaction, cool down to 20-25°C, depressurize, and filter with suction. The filter cake is rinsed with 80g of water, and dried to obtain the intermediate product I, 3-nitro-4-amino - Benzophenone: 160 g, purity 99.8%; impurity 1 purity 0.08%.

[0036] The HPLC chromatographic conditions are as follows: chromatographic column: Kromasil C18 250×4.6mm 5μm, wavelength: 254nm, mobile phase: methanol:0.1% phosphoric acid aqueous solution=60:40, column temperature: 30°C, flow rate: 1.0ml / min.

[0037] Chromatograms such as figure 1 As shown, the results are shown in Table 1 below.

[0038] Table 1

[0039] Intermediate I purity Impurity 1 Remark 99.8％ 0.08％ Other impurities 0.12%

[0040] 2), the interme...

Embodiment 2

[0045] 1), put 3-nitro-4-chloro-benzophenone: 180g, isopropanol: 200g and 20% (mass fraction) ammonia water: 230g into the autoclave, stir and heat up to 70-75°C, heat preservation reaction After 24 hours, the pressure in the kettle reached 0.3-0.35MPa. After the reaction, the temperature was lowered to 20-25°C, depressurized, and suction filtered. The filter cake was rinsed with 80g of water, and dried to obtain the intermediate product I, 3-nitro-4 -Amino-benzophenone: 158 g, purity 98.8%; impurity 1 purity 0.54%.

[0046] HPLC chromatographic condition is the same as embodiment 1, and HPLC chromatogram is as follows image 3 As shown, the results are shown in Table 3.

[0047] table 3

[0048] Intermediate I purity Impurity 1 Remark 98.8％ 0.54％ Other impurities 0.66%

[0049]2), the intermediate product I: 158g and methanol: 500g were added to the beaker and stirred to dissolve, then added to the autoclave, and then added palladium carbon catalys...

Embodiment 3

[0058] 1), put 3-nitro-4-chloro-benzophenone: 180g, N,N-dimethylformamide: 200g and 18% (mass fraction) ammonia water: 270g into the autoclave, stir and heat up to 110 -115°C, heat preservation reaction for 21h, while the pressure in the kettle reaches 0.50-0.55MPa, after the reaction, cool down to 20-25°C, release pressure, filter with suction, rinse the filter cake with 80g of water, and dry to obtain the intermediate product I. 3-nitro-4-amino-benzophenone: 158 g, purity 99.9%; impurity 1 purity 0.06%.

[0059] 2), the intermediate product I: 158g and methanol: 500g were added to the beaker and stirred to dissolve, then added to the autoclave, and then added palladium carbon catalyst: 3.5g, followed by nitrogen replacement 3 times, hydrogen replacement 3 times, and finally filled with hydrogen to 0.15MPa, stir and heat up to 40-45°C, keep warm for 4h. After the reaction, the temperature was lowered to 20-25°C, the pressure was released, the discharge was suction-filtered, ...

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Abstract

The invention discloses a method for synthesizing a mebendazole intermediate 3,4-diamino-benzophenone. By strictly controlling the parameters of the ammoniation process and the hydrogenation process, two impurities in the process: 3-amino- The contents of 4-hydroxy-benzophenone and 3-amino-4-chloro-benzophenone are both reduced to less than 0.05%, which ensures that the product quality is qualified and the total yield of the two-step reaction reaches 90%, which has a very high yield. Industrial production value.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and specifically relates to a method for synthesizing a mebendazole intermediate 3,4-diamino-benzophenone. Background technique [0002] Mebendazole (5-phenylpropionyl-1H-benzimidazol-2-yl) methyl carbamate is a broad-spectrum anthelmintic, which has a significant effect of killing larvae and inhibiting the development of eggs. It is used to prevent and control intestinal parasitic diseases such as hookworms, roundworms, pinworms, whipworms, and fecal nematodes. 3,4-diamino-benzophenone is an important intermediate in the preparation of mebendazole. [0003] The synthesis of 3,4-diamino-benzophenone takes 3-nitro-4-chloro-benzophenone as raw material, and the synthetic method mainly contains following two kinds: (1) with 3-nitro-4-chloro - Benzophenone as the starting material, first react with ammonia water under high pressure to synthesize 3-nitro-4-amino-benzophenone, and then reduce it wit...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C225/22C07C221/00
CPCC07C221/00C07C225/22
Inventor 余志强沈洁徐剑锋曾淼朱家可孙思
Owner SUZHOU KAIYUAN MINSHENG SCI & TECH CORP
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