Synthetic process of metsulfuron-methyl-D3

Abstract

The invention provides a synthesis process of metsulfuron-methyl-D3, comprising the following steps: Step 1), adding a compound I in an ethanol solution of sodium ethoxide to prepare a compound II; Step 2), adding the compound II prepared in the Step 1) into a tetrahydrofuran solution of deuterated sodium methoxide, and refluxing to obtain a compound III; Step 3), suspending a compound IV in anhydrous toluene, dropwise adding a compound V, adding triethylene diamine, and heating to prepare a toluene solution of a compound VI; and Step 4), suspending the compound III prepared in the Step 2) in ethyl acetate in under nitrogen protection, heating and dropwise adding the toluene solution of the compound VI that is obtained in the Step 3), and reacting to prepare the final product metsulfuron-methyl-D3. The invention has the following technical effects: by conversion of the functional group of a relatively-cheap compound I, the compound III is synthesized; although the yield is low, cumbersome multi-step synthesis and the use of a large amount of expensive deuterated methanol are avoided.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a synthesis process of metsulfuron-D3. Background technique [0002] Metsulfuron-methyl is a systemic selective wheat field high-efficiency sulfonylurea herbicide. It is another high-efficiency variety developed by DuPont of the United States after chlorsulfuron-methyl in 1980. Its activity is 3 times higher than that of chlorsulfuron-methyl. The mechanism of action of metsulfuron-methyl is similar to that of chlorsulfuron-methyl. It is absorbed through the roots, stems and leaves of plants, and is rapidly transmitted in the body to inhibit the activity of acetolactate synthase (ALS), resulting in the blockage of biosynthesis of valine and isoleucine, resulting in growth suppressed and died. After being absorbed by the resistant crop wheat, the hydroxylation of the benzene ring is carried out in the body, and the hydroxylated product quickly forms a conjugate with gluc...

AI Technical Summary

Problems solved by technology

[0014] Method 1: The preparation of the intermediate 2-amino-4-methyl-6-methoxy-1,3,5-triazine requires a large amount of deuterated compounds, such as deuterated methanol, which is expensive to synthesize and difficult to prepare in small quantities;

[0015] Method 2: The raw materials are not easy to obtain, and the reaction process requires the use of ammonia, which has high requirements for equipment and operation

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