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Preparation method of herbicide 3-tert-butyl-5-chloro-6-methyluracil

A technology for terpyridine and herbicide, which is applied in the field of preparation of herbicide terpyridine, can solve the problems of unfriendly environment, many synthetic by-products, and high cost, and achieves avoiding serious by-products, simple and safe operation, and low production cost. Effect

Inactive Publication Date: 2019-04-19
ANHUI THERAPY PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The process has the following problems: 1. The preparation of raw material tert-butyl urea requires a large amount of concentrated sulfuric acid and strong alkali, the three wastes are serious, and the environment is not friendly
2. There are many by-products in the synthesis of intermediate V, and the yield is low, resulting in high production costs
[0007] Based on the above-mentioned technical problems, there are problems in the Tetracycline produced according to the existing method, which not only consumes a lot of energy, costs high, causes serious pollution, but also consumes time and labor, which seriously affects the progress of industrial production.

Method used

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  • Preparation method of herbicide 3-tert-butyl-5-chloro-6-methyluracil
  • Preparation method of herbicide 3-tert-butyl-5-chloro-6-methyluracil
  • Preparation method of herbicide 3-tert-butyl-5-chloro-6-methyluracil

Examples

Experimental program
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Effect test

Embodiment 1

[0025] Weigh 130.1g (1.0mol, 1.0eq) of ethyl acetoacetate into a 500mL three-necked reaction flask, add 84.8g (1.1mol, 1.1eq.) of ammonium acetate, 1.6g (0.01mol, 0.01eq) of iron oxide , 650 mL of absolute ethanol, reacted at 60 ° C for 10 h, and the plate reaction was completed, and the yield of ethyl 3-aminocrotonate was 93.4%.

Embodiment 2

[0027] Weigh 130.1g (1.0mol, 1.0eq) of ethyl acetoacetate into a 500mL three-necked reaction flask, add 77.1g (1.0mol, 1.0eq.) of ammonium acetate, 1.6g (0.01mol, 0.01eq) of iron oxide , 650 mL of absolute ethanol, reacted at 60 ° C for 10 h, and the plate reaction was completed, and the yield of ethyl 3-aminocrotonate was 91.5%.

Embodiment 3

[0029] The ethyl 3-aminocrotonate (0.93mol) obtained in Example 1 was cooled to 30°C, and 100.8g (1,2.0eq) of sodium methoxide, 101.4g (1.02mol, 1.1eq) of tert-butyl isocyanate, and nitrogen were added. Protected and heated to 80°C and refluxed for 5h, cooled down, concentrated to remove ethanol, added 500mL of water for beating, and dried the product to obtain 148.3g of intermediate V with a yield of 88%.

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Abstract

The invention discloses a preparation method of herbicide 3-tert-butyl-5-chloro-6-methyluracil. The method comprises the steps that a compound acetoacetic ester is taken as a raw material to react with an ammonia source to generate 3-amino-2-butenoic acid ethyl ester, the 3-amino-2-butenoic acid ethyl ester is reacted with tert-butylisocyanate to generate an intermediate, and the 3-tert-butyl-5-chloro-6-methyluracil is obtained after chlorination is conducted on the intermediate. The method has the advantages that the obtaining of the raw material is easy, the technology is brief, the method is economical and environmentally friendly, and the method is suitable for industrial production.

Description

Technical field: [0001] The invention belongs to the technical field of organic synthesis route design and preparation of raw materials and intermediates, and in particular relates to a preparation method of the herbicide tequadim. Background technique: [0002] Teclodim was developed and marketed by DuPont in 1967. Its chemical name is 5-chloro-3-(1,1-dimethylethyl)-6-methyl-2,4(1H,3H)-dihydroxypyrimidine. Used to control annual weeds, broadleaf weeds and some perennial weeds. Such as goose sausage, crabgrass, Baogai grass, wild mustard, etc. It is mostly used in sugar cane, alfalfa, peach, blackberry, raspberry, pecan, mint, aloe and other crops. [0003] With regard to the preparation method of tequadine, since the product was developed and launched as early as 1966, there are few preparation methods published at home and abroad: [0004] Patent CA716060, DE1803167 and literature [Collection of Czechoslovak Chemical Communications, 1977, vol.42, p718-725] disclose a ki...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/553
CPCC07D239/553
Inventor 彭兵兵任磊孙玉行张红夺柏林张文龙
Owner ANHUI THERAPY PHARMA CO LTD
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