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Preparation method of N-methyl formyl aniline

A technology of methylformanilide and methylaniline, which is applied in the field of synthesis of organic intermediates, can solve the problems of high cost, high pollution or toxicity, and three wastes, and achieve the effect of reducing the amount of feed and low raw material cost

Inactive Publication Date: 2009-07-08
GAOYOU CITY ORGANIC CHEM FACOTRY +1
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  • Abstract
  • Description
  • Claims
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AI Technical Summary

Problems solved by technology

At present, the production method of N-methylformanilide mainly contains: A) adopt methylation of dimethyl sulfate to prepare N-methylformanilide, the raw material toxicity that this method uses is big, and cost is high; B) adopts dimethyl Aniline is oxidized to prepare N-methylformanilide. The cost of the oxidizing agent used in this method is high, and the three wastes are serious
Above-mentioned two kinds of methods cost height, pollution or toxicity are big, for this reason, someone adopts N-methylaniline and formic acid reaction to prepare N-methylformanilide, and this method is the equilibrium reaction of esterification and hydrolysis, needs constantly moving In addition to the water produced in the reaction, a large excess of anhydrous formic acid is required and the reaction is difficult to complete

Method used

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  • Preparation method of N-methyl formyl aniline

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Embodiment 1: the preparation of N-methyl formanilide

[0015] In a 500ml three-necked flask, add boric acid 84g (1.4mol), toluene 200ml, reflux with water, take out 23.5 grams of water (1.3mol) after about 2 hours, cool to 90°C, add 40 grams of formic acid with a content of 88% ( Contain 4.8 grams of water and 0.78mol formic acid) and N-methylaniline 70 grams (0.65mol), insulated under mechanical stirring 90-100 ℃ of reaction 4.5 hours, gas chromatographic follow-up analysis shows that conversion rate is greater than 99%, drops to room temperature, Filter, wash the filter residue with 50ml of toluene, and dry to obtain 82 grams of white solid boric acid, which can be used mechanically. After the filtrates were combined, they were washed with 50 ml of saturated saline, separated into layers, and then the solvent was recovered under reduced pressure to dryness, and the fraction at 80-90 °C / 7mmHg was collected to obtain 81.5 grams of the product, which was a light yellow ...

Embodiment 2

[0021] Embodiment 2: the preparation of 3,4-dimethoxybenzaldehyde

[0022] In a 500ml three-necked flask, add 34.5g (0.25mol) of o-phthalamide and 34.5g (0.225mol) of phosphorus oxychloride, heat to 85°C, and drop into the mixture prepared in Example 1 within 1 hour under stirring. 27 g (0.2 mol) of N-methylformanilide. Insulate and react at 80-90°C for 6 hours, follow the progress of the reaction with TLC, developer ethyl acetate:petroleum ether=1:1. After reacting for 6 hours, the thin layer tracking raw material basically disappeared (developer: ethyl acetate: petroleum ether = 1:3), add 100ml of toluene to dilute, cool down to room temperature, add 100ml of water, stir for 1 hour, and separate layers. After the organic layer was dried over anhydrous sodium sulfate, the solvent was recovered, the residue was rectified by an oil pump, and the 104-108 ° C / 1mmHg fraction was collected to obtain 27.6 g (0.166 mol, gas phase content 98.5%) of the product 3,4-dimethoxybenzaldehy...

Embodiment 3

[0028] Embodiment 3: the preparation of 2,4-dimethoxybenzaldehyde

[0029] In a 500ml three-necked flask, add m-xylylene dimethyl ether 34.5g (0.25mol) and phosphorus oxychloride 34.5g (0.225mol), heat to 85°C, and drop into the mixture prepared in Example 1 within 1 hour under stirring. 27 g (0.2 mol) of N-methylformanilide. Insulate and react at 80-90°C for 3 hours, track the progress of the reaction with TLC, developer ethyl acetate:petroleum ether=1:1. After reacting for 3 hours, the TLC raw material basically disappeared (developer: ethyl acetate:petroleum ether=1:3), add 100ml of toluene to dilute, cool down to room temperature, add 100ml of water and stir for 1 hour, and separate layers. After the organic layer was dried over anhydrous sodium sulfate, the solvent was recovered, the residue was rectified by an oil pump, and the 109-114 ° C / 1mmHg fraction was collected to obtain 25.5 g (0.154 mol, gas phase content 98.2%) of the product 2,4-dimethoxybenzaldehyde. Yield ...

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Abstract

The invention discloses a method for preparing N-methyl formanilide. The prior method adopts N-methylaniline to react with formic acid to prepare the N-methyl formanilide, is balanced reaction of esterification and hydrolysis, and requires continuous removal of water generated during the reaction so as to require superfluous anhydrous formic acid and be difficult to react completely. The method comprises the following steps: firstly, performing refluxing and water-carrying on boric acid in the presence of a solvent which is dissolved in water, and reducing the temperature of the obtained anhydride metaborate which is not subjected to separation to be between 60 and 90 DEG C first; and secondly, directly adding the formic acid and the N-methylaniline into a solution for reaction, and obtaining the N-methyl formanilide. The method adopts the anhydride metaborate as a chemical dewatering agent to remove the water generated during the reaction, strikes the balance, makes the reaction quick and complete, does not require refluxing and water-carrying during synthesis of the N-methyl formanilide, and greatly reduces the feed capacity of the formic acid.

Description

technical field [0001] The invention relates to the synthesis of organic intermediates, in particular to a method for preparing N-methylformanilide. Background technique [0002] N-Methylformanilide (MFA for short) is an important intermediate in organic synthesis. As a raw material for the synthesis of aromatic aldehydes and heterocyclic aldehydes, it is widely used in the Vilsmeier reaction. At present, the production method of N-methylformanilide mainly contains: A) adopt methylation of dimethyl sulfate to prepare N-methylformanilide, the raw material toxicity that this method uses is big, and cost is high; B) adopts dimethyl Aniline is oxidized to prepare N-methylformanilide. The cost of the oxidizing agent used in this method is high, and the three wastes are serious. Above-mentioned two kinds of methods cost height, pollution or toxicity are big, for this reason, someone adopts N-methylaniline and formic acid reaction to prepare N-methylformanilide, and this method is...

Claims

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Application Information

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IPC IPC(8): C07C223/06C07C221/00
Inventor 瞿军沈润溥张符吴宏祥陆文辉龚志娟高启楠陶国峰
Owner GAOYOU CITY ORGANIC CHEM FACOTRY
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