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Method for producing substituted dichloropyrimidine

A technology of dichloropyrimidine and a production method, applied in 4 fields, can solve the problem of not solving the problem of phosphorus-containing wastewater discharge, and achieve the effects of protecting water resources, reducing costs, and good compatibility

Inactive Publication Date: 2009-09-02
江苏常隆化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The use of triphenylphosphine oxide still does not solve the discharge problem of phosphorus-containing wastewater

Method used

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  • Method for producing substituted dichloropyrimidine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] In a well-ventilated fume hood, install a stirring, thermometer, condenser, and vent pipe on a 500-milliliter reaction bottle, and then prepare an exhaust gas absorption and scrubbing bottle, and put liquid alkali in the bottle with a concentration of 10%-20%. Absorb exhaust fumes. Put 15.8g of 2-methylthio-4,6-dihydroxypyrimidine (99%), 250ml of chlorobenzene and 2g of 1-methylimidazole into the flask successively, heat up and reflux, and pass through the airway tube at a rate of about 0.1L / min. Pass through phosgene, follow up with sampling, until high pressure liquid chromatography (HPLC) shows that dihydroxypyrimidine disappears, and it takes about 16 hours to complete. Stop the reaction, drive away excess phosgene with nitrogen, cool, filter, wash the filtrate with water until neutral, dry over anhydrous sodium sulfate and remove chlorobenzene to obtain 18.0 g of 2-methylthio-4,6-dichloropyrimidine , content 96.0%.

Embodiment 2

[0031] In a well-ventilated fume hood, install a stirring, thermometer, condenser, and vent pipe on a 500-milliliter reaction bottle, and then prepare an exhaust gas absorption and scrubbing bottle, and put liquid alkali in the bottle with a concentration of 10%-20%. Absorb exhaust fumes. In the flask, drop into 14.2g 2-methoxy group-4,6-dihydroxypyrimidine (99%), 200ml of 2-dichloroethane and N,N-dimethylaniline 19g successively, heat up and reflux, with about Introduce phosgene through the airway at a rate of 0.1 L / min, take samples and follow up until HPLC shows that dihydroxypyrimidine disappears, which takes about 15 hours to complete. Stop the reaction, drive away the excess phosgene with nitrogen, cool down, remove the solvent dichloroethane, add 300ml of toluene, wash with 100ml of water, separate layers, remove the toluene after drying with anhydrous sodium sulfate, and obtain 2-methoxy - 16.5 g of 4,6-dichloropyrimidine. Content 95.5%.

Embodiment 3

[0033] In a well-ventilated fume hood, install a stirring, thermometer, condenser, and vent pipe on a 500-milliliter reaction bottle, and then prepare an exhaust gas absorption and scrubbing bottle, and put liquid alkali in the bottle with a concentration of 10%-20%. Absorb exhaust fumes. 14.0g of 2-ethyl-4,6-dihydroxypyrimidine (99%), 300ml of dichloromethane and 6.4g of 4-dimethylaminopyridine were successively put into the flask, the temperature was raised to reflux, and the The airway was fed with phosgene, and samples were taken and tracked until HPLC showed that the dihydroxypyrimidine disappeared, which took about 10 hours to complete. Stop the reaction, drive away excess phosgene with nitrogen, cool, filter, wash the filtrate with water until neutral, dry over anhydrous sodium sulfate and remove dichloromethane to obtain 15.6g of 2-ethyl-4,6-dichloropyrimidine . The content is 97.3%.

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PUM

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Abstract

The invention relates to a method for producing 2-subtituted-4,6-dichloropyrimidine, which comprises the following steps of: suspending 2-substitued-4,6-dihydroxypyrimidine in an aprotic polar organic solvent; introducing phosgene into the suspension during stirring in the presence of tertiary amine organic alkali at 30 to 155 DEG C for reaction for 4 to 16 hours; after the reaction is finished, removing excessive phosgene with nitrogen; cooling the reaction product, filtering the product and washing the filtrate till the filtrate is neutral; and drying the filtrate by a drying agent, reclaiming the solvent through distillation or distillation under reduced pressure, and obtaining the 2-subtituted-4,6-dichloropyrimidine. The method for synthesizing the 2-subtituted-4,6-dichloropyrimidine has the advantages that: (1), a tertiary amine catalyst is used to catalyze the reaction and accelerate the reaction; (2), in a reaction process, the phosgene is used as a substitute for phosphorus oxychloride to avoid discharging of phosphor-containing waste water, protect water resource and reduce cost; and (3), the reaction is carried out in the aprotic polar organic solvent, and the yield of the reaction is improved due to good compatibility.

Description

technical field [0001] The invention relates to a production method of substituted dichloropyrimidine, in particular, a production method of 2-substituted 4,6-dichloropyrimidine. Background technique [0002] The 2-substituted 4,6-dichloropyrimidine is a known pyrimidine salicylic acid herbicide (such as: bispyribac-sodium from Japan Combination Chemical Industry Co., Ltd., pyrithiobac-sodium from Japan Combination Chemical Co., Ltd., Syngenta's pyriftalid, etc.), triazoloamide herbicides (such as: Dow Agroscience's diclosulam diclosulam, cloransulam-Methyl, diflorasulam florasulam important Intermediate and amide herbicide safener and dye intermediate - Fenclorim. The known synthesis of 2-substituted 4,6-dichloropyrimidine is based on 2-substituted 4,6-dihydroxypyrimidine as raw material obtained by chlorination. And the 2-substituted 4,6-dihydroxypyrimidine can be easily obtained from the following two routes: 1. by the reaction of alkyl squinium salt and diethyl malonate...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/30C07D239/34C07D239/38
Inventor 陆明若田庆海张中泽张昭荣刘梅
Owner 江苏常隆化工有限公司
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