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A technology of foramsulfuron and methylsulfonamide, which is applied in the field of foramsulfuron-methyl preparation, can solve the problems of environmental pollution, a large amount of waste acetic acid, etc., achieve high formylation reaction yield, avoid impurities, and simple operation
Active Publication Date: 2016-03-16
江苏省农用激素工程技术研究中心有限公司
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[0007] The above two preparation methods all use acetic anhydride and formic acid to form formic anhydride to introduce formyl groups, which
Method used
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Embodiment 1）
[0018] This embodiment is the method for preparing 2-dimethylaminocarbonyl-5-formylaminophenylsulfonamide from 2-dimethylaminocarbonyl-5-aminophenylsulfonamide:
[0019] Add 50.0g of 2-dimethylaminocarbonyl-5-aminophenylsulfonamide, 2.5g of potassium tert-butoxide, and 300mL of ethyl formate into the reaction device, and first stir the reaction at a temperature of 20-25°C 2h, and then raise the temperature to 60±2°C for 5h.
[0020] After the reaction, it was cooled, filtered with suction, and dried to obtain 50.2 g of white solid 2-dimethylaminocarbonyl-5-formylaminophenylsulfonamide, with a yield of 90.0% and a purity of 97.0% (HPLC).
Embodiment 2～ Embodiment 5）
[0022] The method of each embodiment is basically the same as that of Example 1, and the differences are shown in Table 1.
[0023] Table 1
[0024]
Embodiment 6）
[0026] This embodiment is the method for preparing foramsulfuron-methyl from 2-dimethylaminocarbonyl-5-formylaminophenylsulfonamide and phenyl dimethoxypyrimidine carbamate:
[0027] 61.4 g of 2-dimethylaminocarbonyl-5-formylaminophenylsulfonamide, 24 g of triethylamine, 300 mL of acetonitrile, and 65.1 g of 4,6-dimethoxypyrimidine 2-carbamate phenyl Add it to the reaction device, stir and heat up to 50±2°C, and react for 5h.
[0028] After the reaction, 200mL of acetonitrile was distilled off under reduced pressure, cooled, an appropriate amount of ice water was added, and then hydrochloric acid was added dropwise to adjust the pH=3, suction filtered, washed with water, and dried to obtain 92.2 g of off-white solid foramsulfuron, with a yield of 90.0% , with a purity of 95.3% (HPLC).
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Abstract
The invention discloses a preparation method of foramsulfuron. The preparation method of foramsulfuron comprises the following steps: firstly carrying out reaction on 2-dimethyl amino carbonyl-5-aminophenyl sulfonamide and ethyl formate in presence of a basic catalyst to generate 2-dimethyl amino carbonyl-5-formyl aminophenyl sulfonamide, and then carrying out condensation reaction with dimethoxy pyrilamine phenyl formate, so that foramsulfuron is obtained, wherein a molar ratio of 2-dimethyl amino carbonyl-5-aminophenyl sulfonamide to ethyl formate is 1:(10-30), the basic catalyst is potassium tert-butoxide, and amount of the added basic catalyst is 0.05-0.1 time of the weight of 2-dimethyl amino carbonyl-5-aminophenyl sulphonamide. The preparation method of foramsulfuron has the advantages that ethyl formate is adopted for introducing formyl, pollution of waste acetic acid is not produced, production of acetyl impurity also can be avoided, a high-purity formylation product also can be obtained, and higher formylation reaction yield can be obtained as potassium tert-butoxide is adopted as the basic catalyst.
Description
technical field [0001] The invention belongs to the technical field of fine chemicals, and in particular relates to a preparation method of foramsulfuron-methyl. Background technique [0002] Foramsulfuron-methyl is a new type of ultra-efficient sulfonylurea herbicide developed by Bayer AG of Germany. It is mainly used to control annual grasses and broad-leaved weeds in corn fields. Its chemical name is: 1-(4,6-dimethoxy Pyrimidin-2-yl)-3-(2-dimethylaminocarbonyl-5-formamidophenylsulfonyl)urea, the structural formula is as follows: [0003] . [0004] Existing preparation method mainly contains following two kinds: [0005] (1) First mix acetic anhydride and formic acid to generate formic anhydride, then react formic anhydride with 2-dimethylaminocarbonyl-5-aminophenylsulfonamide to prepare 2-dimethylaminocarbonyl-5-formylamino Phenylsulfonamide, and finally, foramsulfuron is obtained through the condensation reaction of 2-dimethylaminocarbonyl-5-formylaminophenylsulfon...
Claims
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