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Preparation method of 4-nitro-3-trifluoromethylaniline

A technology of trifluoromethylaniline and trifluoromethylacetaniline, which is applied in the field of preparation of 4-nitro-3-trifluoromethylaniline, can solve the problems of positional isomers, difficult refining, low yield, etc. , to achieve the effect of simple refining, high reaction yield and high yield

Inactive Publication Date: 2011-06-15
天津均凯农业科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is acetic anhydride as a precursor reagent, and mixed acid is used for nitration, and there are positional isomers in the reaction product, and there are difficulties in refining and low yield (see J.Am.Chem.Soc.1951, 73, 3579)

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] 1.0 kg of m-trifluoromethylaniline was dissolved in 10 L of toluene, the temperature was controlled at 50°C, and 0.55 kg of acetyl chloride was added dropwise. After the dropwise addition, the temperature was raised to 55°C for 5 hours of reaction. After cooling, a white solid precipitated out and was filtered to obtain 0.98 kg of m-trifluoromethylacetanilide with a yield of 78%.

Embodiment 2

[0025] 1.0 kg of m-trifluoromethylaniline was dissolved in 20 L of cyclohexane, and the temperature was controlled at 50° C., and 0.55 kg of acetyl chloride was added dropwise. After the dropwise addition, the temperature was raised to 55° C. for 5 hours. After cooling, a white solid precipitated out and was filtered to obtain 1.1 kg of m-trifluoromethylacetanilide with a yield of 91%.

Embodiment 3

[0027] 1.0 kg of m-trifluoromethylaniline was dissolved in 20 L of chlorobenzene, the temperature was controlled at 50°C, and 0.55 kg of acetyl chloride was added dropwise. After the dropwise addition, the temperature was raised to 55°C for 5 hours of reaction. After cooling, a white solid precipitated out and was filtered to obtain 0.87 kg of m-trifluoromethylacetanilide with a yield of 69%.

[0028] Part II: Preparation of 4-nitro-3-trifluoromethylacetanilide

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PUM

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Abstract

The invention provides a preparation method of 4-nitro-3-trifluoromethylaniline. The preparation method comprises the following steps: nitrifying m-trifluoromethyl)phenyl]acetamide obtained by reacting m-(trifluoromethyl)aniline with acetylchloride in a non-protic solvent so as to obtain 4-nitro-3-trifluoromethylacetanilide; and removing acetyl protection in ethanol solution by potassium carbonate so as to obtain the 4-nitro-3-trifluoromethylaniline. The preparation method has the advantages that reaction yield is high, generated three wastes are less, reaction is easy to control, impurities in product position positional isomers are less, yield is high, rectification is simple and the like.

Description

technical field [0001] The invention belongs to a flutamide intermediate, in particular to a preparation method of 4-nitro-3-trifluoromethylaniline. Background technique [0002] Flutamide is a non-steroidal androgen antagonist, which was first designed and synthesized by Schering-Plough Company in the United States. It was first listed in the United States as a drug for treating prostate cancer in 1989. Its chemical name is 2-methyl-N-[4- Nitro-3-(trifluoromethyl)phenyl]propionamide is an anilide drug. Because flutamide itself does not have any hormonal activity, it is effective in treating prostate diseases, has no effect on cardiovascular disease, and can maintain the patient's sexual function. It has gradually become a common drug for treating prostate cancer and benign prostatic hyperplasia in European and American countries. It is used for non-prostatic diseases related to androgen, and the incidence of adverse reactions of flutamide is low, and the patient can tolera...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/46C07C209/62
Inventor 尚振华栗晓东张慧丽
Owner 天津均凯农业科技有限公司
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