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A kind of preparation method of 2-chloro-n-(4-fluorophenyl)-n-isopropylacetamide

A technology of isopropylacetamide and fluorophenyl, which is applied in the field of preparation of 2-chloro-N--N-isopropylacetamide, can solve the problems of high raw material preparation cost, difficult removal, and large amount of waste water. Achieve the effect of simple operation, less corrosion of equipment and mild reaction

Inactive Publication Date: 2016-05-18
ORIENTAL LUZHOU AGROCHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] There are many problems in the existing technology for preparing 2-chloro-N-(4-fluorophenyl)-N-isopropylacetamide, such as high raw material preparation cost, large amount of waste water, and impurities that are difficult to remove.

Method used

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  • A kind of preparation method of 2-chloro-n-(4-fluorophenyl)-n-isopropylacetamide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Add 154.7g of N-isopropyl-4-fluoroaniline, 102.2 g of triethylamine and 400 mL of toluene to a 1000 mL three-necked flask equipped with mechanical stirring, a thermometer and a constant pressure dropping funnel, and add 114 g of chloroacetyl chloride dropwise at room temperature, Add dropwise for 1.5 hours, continue to react for 4 hours after dropping, add 150mL of water to wash, separate triethylamine hydrochloride aqueous solution, wash the organic phase with water, remove the solvent to obtain 228.7g 2-chloro-N-(4-fluorophenyl )-N-isopropylacetamide, purity 98.4%, yield 98%

[0018] 1 HNMR (400MHz, CDCl 3 ),&:7.16(m,2H),7.15(m,2H),4.97(m,1H),4.67(s,2H),1.07(d,J=5.2Hz,6H).

[0019] Add 40g sodium hydroxide in triethylamine hydrochloride aqueous solution, stir 10 minutes, separate liquid, organic layer adds 40g sodium hydroxide drying, after drying 12 hours, filter, obtain 97.3g triethylamine, recovery rate 95.2%, The sodium hydroxide filter cake is used for the nex...

Embodiment 2

[0021] Add 154.7g of N-isopropyl-4-fluoroaniline, 102.2g of triethylamine (97.3g from the previous batch) and 450mL of xylene to a 1000mL three-necked flask equipped with mechanical stirring, a thermometer and a constant pressure dropping funnel. Add 114g of chloroacetyl chloride dropwise at room temperature for 1.5 hours, continue to react for 4 hours after dropping, add 150mL of water to wash, separate triethylamine hydrochloride aqueous solution, wash the organic phase with water, remove the solvent to obtain 228.5g of 2-chloro -N-(4-fluorophenyl)-N-isopropylacetamide, purity 98.6%, yield 98.1%.

[0022] Add 40g of the previous batch of sodium hydroxide filter cake to triethylamine hydrochloride aqueous solution, stir for 10 minutes, separate liquids, add 40g of sodium hydroxide to the organic layer for drying, after drying for 12 hours, filter to obtain 98g of triethylamine, recover The rate is 95.9%, and the sodium hydroxide filter cake is used for the treatment of the tr...

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Abstract

The invention discloses a method for preparing 2-chloro-N-(4-fluorophenyl)-N-isopropylacetamide. The method comprises the steps as follows: N-isopropyl-4-fluoroaniline and chloroacetyl chloride are taken as raw materials, triethylamine is taken as an acid-binding agent, a reaction is performed under the mild condition, and 2-chloro-N-(4-fluorophenyl)-N-isopropylacetamide is obtained. Triethylamine is recovered with a follow-up simple technology, so that N-alkylate impurities are effectively avoided; and the technology mainly has numerous advantages as follows: the reaction is mild, the operation is simple and convenient, the equipment corrosiveness is small, the yield and the purity are high, and the method is suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of organic synthesis of acetamide. More specifically, it relates to a preparation method of 2-chloro-N-(4-fluorophenyl)-N-isopropylacetamide. Background technique [0002] Amides are a very important class of herbicides, flufenacet, 2-(1,3-benzothiazole-2-oxyl)-N-(4-fluorophenyl)-N-isopropylacetamide are Two of them, 2-chloro-N-(4-fluorophenyl)-N-isopropylacetamide, were synthesized from flufenacet and 2-(1,3-benzothiazole-2-oxyl)- The key intermediate of N-(4-fluorophenyl)-N-isopropylacetamide, and its synthesis method has received extensive attention. [0003] U.S. Patent No. 4,453,965 discloses that chloroacetyl chloride and N-isopropyl-4-fluoroaniline are raw materials, and pyridine is an acid-binding agent to synthesize 2-chloro-N-(4-fluorophenyl)-N-isopropylacetamide, The reaction conditions are mild and the yield is high, but the price of pyridine is high and the recovery of pyridine hydrochloride produced i...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C233/15C07C231/02
Inventor 苏叶华蔡国平刘维付学华李益声陈邦池
Owner ORIENTAL LUZHOU AGROCHEM
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