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Preparation method of oxaziclomefone

A technology of oxaziclozone and its compound, which is applied in the field of preparation of oxaziclozone, can solve the problems of low yield and cumbersome synthesis process, and achieve the effects of high yield, shortened synthetic route, and good stability of raw materials

Active Publication Date: 2018-10-09
SHANDONG CYNDA CHEM
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] The object of the present invention is to provide a kind of preparation method of oxaziclodione in order to overcome the defect that the synthetic process of oxaziclozone is loaded down with trivial details in the prior art, yield is low, and this method comprises the following steps: in paraformaldehyde and catalyzer In the presence of the compound represented by formula (1) or formula (2) and 1-methyl-1-(3,5-dichlorophenyl) ethylamine represented by formula (3) is reacted;

Method used

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  • Preparation method of oxaziclomefone
  • Preparation method of oxaziclomefone
  • Preparation method of oxaziclomefone

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preparation example Construction

[0017] The invention provides a method for preparing oxaziclozone, the method comprising the following steps: in the presence of paraformaldehyde and a catalyst, combining the compound represented by formula (1) or formula (2) with the compound represented by formula (3) Shown 1-methyl-1-(3,5-dichlorophenyl) ethylamine reacts;

[0018]

[0019] Among them, R is C 1 -C 5 the alkyl group;

[0020] The general formula of the paraformaldehyde is—(CH 2 O) n —, n is an integer of 2-100;

[0021] The catalyst contains alcohol, alkali and free radical inhibitor.

[0022] In the present invention, the compounds represented by the formula (1) and formula (2) are isomers of each other, and both are keto and enol isomers. The C 1 -C 5 The alkyl group includes, but is not limited to: at least one of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl and tert-amyl . Preferably, R is methyl or ethyl.

[0023] In the present invention, the par...

Embodiment 1

[0039] This example is used to illustrate the preparation method of oxaziclozone of the present invention

[0040] Paraformaldehyde (0.88g), ethanol (1.35g), triethylamine (0.02g), Na 2 S (0.015 g), 1-methyl-1-(3,5-dichlorophenyl)ethylamine (2 g) were added to a 200 mL reaction flask, and 100 mL of xylene was added thereto. After the reaction solution was heated to reflux for 5 h under stirring, 1-acetophenethyl ester (2.1 g) was added thereto and refluxed at 180° C. for 6 h. After the reaction was completed, the system was cooled to room temperature, xylene was removed under reduced pressure, and the obtained residue was recrystallized from petroleum ether (15 mL). The solid obtained by recrystallization was suction-filtered and vacuum-dried to obtain 3 g of oxaziclozone as a white solid with a yield of 81%.

[0041] 1 H NMR (400MHz, CDCl 3 )δ7.27 (m, 8H), 5.45 (s, 2H), 1.89 (s, 3H), 1.64 (s, 6H).

Embodiment 2

[0043] This example is used to illustrate the preparation method of oxaziclozone of the present invention

[0044] Paraformaldehyde (1.47g), methanol (0.5g), N-methylpyrrole (0.4g), hydroquinone (0.015g), 1-methyl-1-(3,5-dichlorophenyl ) Ethylamine (2g) was added into a 200mL reaction flask and 100mL of toluene was added thereto. After the reaction solution was heated to reflux for 5 h under stirring, 1-acetylbenzyl ester (4.7 g) was added thereto and refluxed at 110° C. for 10 h. After the reaction was completed, the system was cooled to room temperature, and the toluene was removed under reduced pressure, and the obtained residue was recrystallized from petroleum ether (15 mL). The solid obtained from the recrystallization was suction filtered and vacuum dried to obtain 2.95 g of oxaziclozone as a white solid with a yield of 80%.

[0045] 1 H NMR (400MHz, CDCl 3 )δ7.27 (m, 8H), 5.45 (s, 2H), 1.89 (s, 3H), 1.64 (s, 6H).

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Abstract

The invention relates to the field of preparation of oxaziclomefone, and discloses a preparation method of the oxaziclomefone. The preparation method comprises the following step: in the presence of paraformaldehyde and a catalyst, performing a reaction on a compound shown as a formula (1) or a formula (2) with 1-methyl-1-(3,5-dichlorophenyl) ethylamine shown as a formula (3), wherein R is C1-C5 alkyl; the paraformaldehyde adopts a general formula -(CH2O)n-, and n is an integer from 2 to 100; and the catalyst cpmprises alcohol, alkali and a radical polymerization inhibitor. By adopting the preparation method, the synthesis route of the oxaziclomefone is shortened, raw materials are good in stability, and the yield of the oxaziclomefone is high.

Description

technical field [0001] The present invention relates to the field of preparation of oxazicloim, in particular to a preparation method of oxazicloim. Background technique [0002] Oxazimidone is an important herbicide in paddy fields, which is widely used to control barnyardgrass and other important grass weeds and some broad-leaved weeds. [0003] At present, the synthesis of oxaziclozone mainly adopts the following two synthetic routes. The first synthetic route adopts that the ethyl 1-acetophenacetate shown in the formula (5) and the N-methylene-1-methyl-1-(3,5) shown in the formula (6) -Dichlorophenyl)ethylamine is reacted under the condition of reflux of xylene as the solvent to prepare oxaziclomozone. The preparation of oxaziclozone using this route requires the preparation of N-methylene- 1-Methyl-1-(3,5-dichlorophenyl)ethanamine (see US5696054A). Therefore, this route is a two-step reaction, the first step is carried out in an aqueous solution, and the second step...

Claims

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Application Information

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IPC IPC(8): C07D265/06
CPCC07D265/06
Inventor 席真王现全王大伟李凯邹亚波
Owner SHANDONG CYNDA CHEM
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