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ChemicalBook CAS DataBase List Monolinuron
1746-81-2

Monolinuron synthesis

4synthesis methods
The industrial synthesis of monolinuron begins with the preparation of 4-chloroaniline, which serves as the aromatic base. This compound undergoes a condensation reaction with methyl isocyanate or dimethylcarbamoyl chloride to form the substituted urea backbone. The methoxy group is introduced via methylation using agents such as dimethyl sulphate or methyl iodide. These reactions are typically carried out in organic solvents like acetone or toluene under controlled temperature and pH conditions to ensure high yield and purity. After synthesis, the crude product is purified through crystallisation or solvent extraction.
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Yield:1746-81-2 79%

Reaction Conditions:

with triethylamine in toluene at -5 - 20;Large scale;Green chemistry;Solvent;Reagent/catalyst;Temperature;

Steps:

1-6 Example 2
Dimethylhydroxylamine hydrochloride (718.8 g) was dissolved in 7 liters of toluene and cooled to about 0 °C. (low temperature minus 5 ° C, high temperature positive 5 ° C). Triethylamine (1200 g) was added portionwise to the stirred solution. The temperature control is less than 20 ° C, p-chlorophenyl isocyanate (943 g) is slowly added, and the addition is completed within about 2 hours. After the addition is completed, the temperature is raised to room temperature, and stirring is continued for 5-12 hours. The reaction solution was cooled to 0-10 ° C, incubated for 3-4 hours, solids were precipitated, filtration was started, and a solid was collected. The above solid is dissolved in methanol or dichloromethane, decolorized with activated carbon, and then concentrated to remove most of the solvent, and the temperature is lowered to 0-10 ° C, and white crystals are gradually precipitated. The solid is collected by centrifugation and dried to obtain a product.That is, the monolinuron 1250 grams, the yield of 79%.

References:

Wuhan Luohua Technology Co., Ltd.;Ji Changpeng;Zhang Baohui;Cai Guangan CN109438287, 2019, A Location in patent:Paragraph 0040-0075

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