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Method for preparing glufosinate-ammonium hydantoin intermediate and analogue thereof
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An intermediate, glufosinate-ammonium technology, applied in the field of preparation of glufosinate-ammonium hydantoin intermediates and analogs, can solve the problems of low efficiency, cumbersome reaction, high production cost, etc.
Active Publication Date: 2021-03-30
LIER CHEM CO LTD +1
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Problems solved by technology
In the prior art, the preparation method of glufosinate-ammonium generally has the problems of complicated reactions, low efficiency and high production costs
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Embodiment 1
[0095]
[0096] In a 500mL three-neck flask, add L-homoserine (140g, 1.18mol), urea (106g, 1.76mol), water (250mL), heat up to an internal temperature of 100°C for 8 hours, cool to room temperature, and spin the water dry , beating with methanol (100mL), washed three times with methanol (50mL x 3), and dried to obtain 181.7g of white crystal 4-hydroxy-2-ureidobutyric acid, yield 95%, HPLC purity 96%, and it was detected as exogenous racemic mixture.
[0097] The product structure analysis data is as follows: MS (ESI): m / z [M+H] + calcd for C 5 h 11 N 2 o 4 :163.06; found: 163.1.
Embodiment 2
[0099]
[0100] In a 250mL three-necked flask, add the 4-hydroxy-2-ureidobutanoic acid (28g, 172.7mmol) prepared in Example 1, 18% HCl (57.6mL, 345.4mmol), heat and stir to raise the temperature to 90°C for reaction 6h, cooled to room temperature, and the water was spin-dried to obtain a white solid, which was washed with ethanol (100mL x 3), and dried to obtain a white solid 5-(2-hydroxyethyl)imidazolidine-2,4-dione 24 g, 97% yield, 97% HPLC purity, detected as a racemic mixture.
[0104] 13 C NMR (D 2 O, 100MHz) δ: 179.0, 159.3, 57.4, 56.2, 32.7.
Embodiment 3
[0106]
[0107] In a 250mL three-necked flask, add the 4-hydroxy-2-ureidobutyric acid (28g, 172.7mmol) prepared in Example 1, 18%H 2 SO 4 (57.6mL, 345.4mmol), heat and stir to raise the temperature to 100°C for 4 hours, cool to room temperature, spin off part of the water, cool down to 0°C to crystallize, wash the white solid with ethanol (50mL x 3), and dry , 23.6 g of white solid 5-(2-hydroxyethyl)imidazolidine-2,4-dione was obtained, the yield was 95%, the HPLC purity was 99%, and it was detected as a racemic mixture.
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Abstract
The invention relates to a method for preparing glufosinate-ammoniumhydantoin intermediate and analogue thereof. The method comprises the following steps: carrying out a reaction on a compound as shown in a formula (II) or a salt thereof, enantiomers or a mixture of enantiomers in all proportions, and a compound as shown in a formula (III) to obtain a compound as shown in a formula (IV); performing intramolecular condensation on the compound shown in the formula (IV) to obtain a compound shown in a formula (V); reacting the compound shown in the formula (V) with a halogenating agent to obtaina compound shown in a formula (I); and carrying out a rearrangement reaction on the compound shown in the formula (I) or salt, enantiomer or a mixture of enantiomers in all proportions thereof and acompound shown in a formula (VII) to convert into a compound shown in a formula (VI). When the hydantoin intermediate and the analogue thereof are used for synthesizing glufosinate-ammonium, the problems of high cost, low efficiency and the like in the prior art can be solved, and the method has the advantage of high cost.
Description
technical field [0001] The invention relates to a method for preparing glufosinate-ammoniumhydantoin intermediates and analogues. Background technique [0002] Glufosinate-ammonium is a broad-spectrum organophosphate contact herbicide successfully developed by Hearst in the 1980s. Glufosinate-ammonium is a glutamine synthesis inhibitor, and its systemic effect is not strong. Glyphosate is different from root-killing. Glufosinate-ammonium kills leaves first, and then conducts transpiration in plantxylem through planttranspiration. Its quick-acting property is between paraquat and glyphosate, and it is a non-selective contact herbicide. In the prior art, the preparation method of glufosinate-ammonium generally has the problems of complicated reactions, low efficiency and high production costs. Contents of the invention [0003] The invention provides a method for preparing formula (I) glufosinate-ammonium hydantoin intermediate and its analogs: [0004] [0005] or a...
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