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Preparation of 4,6-dimethoxy-2-((phenoxy carbonyl) amino) pyrimidine

A technology of phenoxycarbonyl and dimethoxy, which is applied in the field of preparing intermediate compounds useful in the preparation of herbicides, and can solve problems such as no disclosure content

Inactive Publication Date: 2002-08-21
EI DU PONT DE NEMOURS & CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] References US 5,102,444 and US 5,017,212 disclose the preparation and use of the same DPAP for the preparation of sulfonylurea herbicides, but do not disclose the content of the present invention

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] A 500 mL flask was charged with 23.8 g (0.154 mol) of 2-amino-4,6-dimethoxypyrimidine, 29.1 g (0.240 mol) of N,N dimethylaniline and 110 mL of 1,4-dioxane. The mixture was cooled to 5°C with an ice bath. Then 37.58 g (0.24 mol) of phenyl chloroformate were added dropwise, while keeping the temperature of the reaction mixture below 20°C. The reaction mixture was stirred at room temperature (20 to 25°C) for 16 hours before cooling back to 5°C. To this reaction mixture was added water 325 mL; the temperature was kept below 20°C during the addition. The reaction mixture (as a slurry) was filtered and the solids were washed twice with an additional 50 mL of water. The solids were dried by suction through the filter. The weight of the recovered solid having a melting point of 117-120°C was 34,24 g. Calculated yield was 81%, uncorrected for purity.

Embodiment 2

[0018] The procedure of Example 1 was repeated except that 110 mL of tetramethylurea was used instead of 1,4-dioxane. The weight of the recovered solid, mp 117-120°C, was 35.77 g, for a calculated yield of 85%, uncorrected for purity.

Embodiment A

[0019] Embodiment A (comparison)

[0020] This example illustrates the use of tetrahydrofuran (THF) solvent with the N,N-dimethylaniline acid acceptor. Yields are lower than Examples 1 and 2. Judging by the lower melting point range, the product purity is also low.

[0021] A 500 mL beaker was charged with 23.8 g of 2-amino-4,6-dimethoxypyrimidine, 29.10 g of N,N-dimethylaniline and 110 mL of THF. The mixture was cooled to 5°C with an ice bath, and 37.58 g of phenyl chloroformate were slowly added while maintaining the temperature below 20°C. After stirring at room temperature (20°-25°C) for 16 hours, the mixture was cooled to 5°C. To this reaction mixture was added 360 mL of water while maintaining the temperature below room temperature. The reaction mixture (as a slurry) was filtered and the solid was washed with two 50 mL portions of water. The solids were dried on the filter and then placed in a tray to air dry. The recovered solid, having a meltin...

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PUM

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Abstract

The invention relates to a Process for preparing 4,6-dimethoxy-2-((phenoxycarbonyl)amino)pyrimidine comprising reacting 2-amino-4,6-dimethoxy pyrimidine and phenyl chloroformate in an inert solvent in the presence of an acid receptor.

Description

Background of the invention [0001] The present invention relates to a process for the preparation of intermediate compounds useful in the preparation of herbicides. More specifically, the present invention relates to an improved process for the preparation of 4,6-dimethoxy-2-((phenoxycarbonyl)amino)-pyrimidine (hereinafter referred to as "DPAP"), which is used for the preparation of sulfonyl Intermediates of urea herbicides. [0002] Intermediates for herbicides are preferably free of substantial amounts of impurities, especially impurities which would themselves be carried over to the final herbicide. Impurities in agricultural products are checked by strict regulations and subject to strict restrictions. Advantageous methods of preparing intermediates not only facilitate high yields but also produce the desired intermediates in high purity so that little, preferably no, further purification is required. It is therefore an object of the present invention to provide a proce...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/52
CPCC07D239/52
Inventor J·J·罗卡
Owner EI DU PONT DE NEMOURS & CO
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