Method for producing 2-methyl-4-methylamino-6-methoxyl-1,3,5-triazine

A technology of methoxyl group and methylamino group, applied in the direction of organic chemistry, etc., can solve the problems of low total process yield, difficulty in popularization and application, and high production cost

Inactive Publication Date: 2004-11-17
NANJING UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the total yield of the foreign technology is not high, which makes

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Preparation of 2-methyl-4,6-dichloro-1,3,5-triazine

[0017] Add 9.6g of magnesium chips, 160mL of toluene, 80mL of tetrahydrofuran, 10mL of hexane and a grain of iodine into a 500ml four-necked round-bottomed flask equipped with a thermometer, a mechanical stirrer, a vent tube and a spherical condenser, and blow nitrogen into it. Slowly raise the temperature to 50-60°C under stirring, pass in dry methyl chloride gas (0.6g / min), the reaction of magnesium chips is complete, continue to react for 0.5h, and cool down for later use. The yield of the obtained methylmagnesium chloride Grignard reagent is greater than 97%.

[0018] Add 72.5g of cyanuric acid chloride and 300mL of toluene. Stirring was started, nitrogen gas was introduced, and the above-mentioned methylmagnesium chloride Grignard was slowly added dropwise into the four-necked flask at about 0°C. After dropping, react at 0°C for another 0.5h, then warm up to room temperature, and react at room temperature fo...

Embodiment 2

[0024] Preparation of 2-methyl-4,6-dichloro-1,3,5-triazine

[0025] Add 9.6g magnesium chips, 100mL toluene, 60mL tetrahydrofuran, 60mL petroleum ether and 1ml iodomethane into a 500ml four-neck round bottom flask equipped with a thermometer, a mechanical stirrer, a vent tube and a spherical condenser. The atmosphere was replaced with nitrogen gas. Then, slowly raise the temperature to between 35°C and 50°C under stirring, pass through dry methyl chloride gas (60g / min), after the reaction of magnesium chips is completed, reflux for 1.5h, and cool down for later use. The yield of the obtained methylmagnesium chloride Grignard reagent is greater than 96%.

[0026] Add 72.5g cyanuric acid chloride and 300ml of toluene. Stirring was started, nitrogen gas was introduced, and then, at about 10°C, the above-mentioned methylmagnesium chloride Grignard test solution was slowly added dropwise into the four-necked flask. After dropping, keep warm for 0.5h, warm up to room temperatur...

Embodiment 3

[0029] Preparation of 2-methyl-4,6-dichloro-1,3,5-triazine

[0030] Add 9.6g of magnesium chips, 60mL of benzene, 170mL of 1,4-dioxane, 80mL of octane and a small amount of benzyl chloride into a 500ml four-neck round bottom flask equipped with a thermometer, a mechanical stirrer, a vent tube and a spherical condenser . The atmosphere was replaced with nitrogen gas. Then, slowly raise the temperature to between 5°C and 15°C under stirring, pass in dry methyl chloride gas (60g / min), after the reaction of magnesium chips is completed, reflux for 0.5h, and cool down for later use. The yield of the obtained methylmagnesium chloride Grignard reagent is greater than 87%.

[0031]Add 72.5g cyanuric acid chloride and 300ml of toluene. Stirring was started, nitrogen gas was introduced, and then, at about -10°C, the above-mentioned methylmagnesium chloride Grignard test solution was slowly added dropwise into the four-necked flask. After dropping, keep warm for 1.5h, then warm up ...

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Abstract

A process for preparing 2-methyl-4- methylamino-6- methoxyl-1, 3, 5- triazine, realized by reacting magnesium with methyl chloride in ether - aromatic hydrocarbon - alkane mixed solvent to obtain methylmagnesium chloride, then carrying out methylation with cyanuryl chloride, and proceeding methoxylation and methylaminolation with the action of quaternary ammonium salt phase transition catalyst.

Description

technical field [0001] The invention belongs to the field of organic chemistry and relates to a preparation method of compound 2-methyl-4-methylamino-6-methoxy-1,3,5-triazine. Background technique [0002] 2-Methyl-4-methylamino-6-methoxy-1,3,5-triazine is the preparation of 2-[4-methoxy-6-methyl-1,3,5-triazine-2 -An important intermediate of methylcarbamoylamino]benzoate (commonly known as tribenuron-methyl). Tribesulfuron-methyl is a high-efficiency, low-toxicity sulfonylurea herbicide developed by DuPont in the early 1980s. Synthesis is inhibited, cell division is prevented, shoot and root growth is inhibited, and weeds die. Field tests show that trisulfuron-methyl herbicide has special effects on annual and perennial broad-leaved grasses, and the dosage is very small, only 0.5-0.7g per mu. It has low toxicity and short residual period, and is suitable for wheat and next crops Safety. Compared with other sulfonylurea herbicides used in wheat fields such as chlorsulfur...

Claims

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Application Information

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IPC IPC(8): C07D251/46
Inventor 朱红军韩邦友王锦堂宋广亮钱圣利陈圣春徐守林
Owner NANJING UNIV OF TECH
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