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Preparation method of pyridylquinazoline

A technology of pyridine quinazoline and halomethylpyridine, which is applied in the field of preparation of pyridine quinazoline, can solve problems such as difficulty in industrial production, 3-pyridine formaldehyde is not suitable for storage, etc., so as to reduce raw material cost, production cost, and yield high rate effect

Inactive Publication Date: 2019-05-03
湖南速博生物技术有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Similar to the synthesis method disclosed in JP2001342186, this method has a two-step catalytic hydrogenation reaction and uses sodium hydride, which has strict requirements on the water content of the reaction system. In addition, 3-pyridinecarbaldehyde is not suitable for storage, and industrial production is more difficult.

Method used

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  • Preparation method of pyridylquinazoline
  • Preparation method of pyridylquinazoline

Examples

Experimental program
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Effect test

Embodiment 1

[0026] Add 66.9g (0.20mol) of 2-methyl-4-(perfluoropropan-2-yl)phenyl carbamate, 12.9g of sodium methoxide (0.24mol), and 330g of toluene into the A 500mL three-neck flask with a thermometer, after reflux for 0.5 hours, added 24.5g (0.24mol) acetic anhydride, and then refluxed for 4 hours. After the reaction was completed, the sodium carbonate aqueous solution was washed to neutrality, and the water layer was separated, and the oil layer was distilled under reduced pressure to obtain 71.5 g methyl acetyl (2-methyl-4-(perfluoropropan-2-yl)-phenyl) carbamate, content 95.5% (LCD external standard), yield 91%.

[0027] Add 71.5g (0.182mol) of methylacetyl (2-methyl-4-(perfluoropropan-2-yl)-phenyl) carbamate and 285g of chlorobenzene into the 1. A 1000mL three-necked flask with a ventilation device, control the reaction temperature at 55°C, feed 15.5g (0.218mol) chlorine gas, control the feed time for 10h, and continue the reaction for 2h. After the reaction is completed, wash the ...

Embodiment 2

[0031] Add 66.9g (0.20mol) of 2-methyl-4-(perfluoropropan-2-yl)phenyl carbamate, 12.9g of sodium methoxide (0.24mol), and 400g of toluene into the A 500mL three-neck flask with a thermometer, after reflux for 0.5 hours, added 24.5g (0.24mol) acetic anhydride, and then refluxed for 4 hours. After the reaction was completed, the sodium carbonate aqueous solution was washed to neutrality, and the water layer was separated, and the oil layer was distilled under reduced pressure to obtain 71.5 g methyl acetyl (2-methyl-4-(perfluoropropan-2-yl)-phenyl) carbamate, content 95.8% (LC external standard), yield 91.3%.

[0032]Add 71.5g (0.183mol) of methylacetyl (2-methyl-4-(perfluoropropane-2-yl)-phenyl) carbamate and 285g of chlorobenzene into the 1. A 1000mL three-necked flask with a ventilation device, control the reaction temperature at 60°C, feed 15.6g (0.220mol) chlorine gas, control the feeding time for 10h, and continue the reaction for 2h. After the reaction is completed, wash ...

Embodiment 3

[0036] Add 66.9g (0.20mol) of 2-methyl-4-(perfluoropropan-2-yl)phenylcarbamate, 12.9g of sodium methoxide (0.24mol), and 465g of toluene into the A 500mL three-neck flask with a thermometer, after reflux for 0.5 hours, added 24.5g (0.24mol) acetic anhydride, and then refluxed for 4 hours. After the reaction was completed, the sodium carbonate aqueous solution was washed to neutrality, and the water layer was separated, and the oil layer was distilled under reduced pressure to obtain 71.5 g methylacetyl (2-methyl-4-(perfluoropropan-2-yl)-phenyl) carbamate, content 95.5% (LC external standard), yield 91%.

[0037] Add 71.5g (0.182mol) of methylacetyl (2-methyl-4-(perfluoropropane-2-yl)-phenyl) carbamate and 430g of chlorobenzene into the 1. A 1000mL three-necked flask with a ventilation device, control the reaction temperature at 55°C, feed 15.5g (0.218mol) chlorine gas, control the feed time for 10h, and continue the reaction for 2h. After the reaction is completed, wash the oi...

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Abstract

The invention discloses a preparation method of pyridylquinazoline. The method uses 2-methyl-4-(perfluoropropan-2-yl)phenylcarbamate as a raw material, acetylation is performed, chlorination is performed, hydration hydrate ring formation is performed, and finally reaction is performed on the ring-formed compound and 3-halomethylpyridine to obtain the pyridylquinazoline with a content of 97.5%-98.5%, wherein the total yield is 59.0-63.0% (calculated based on the 2-methyl-4-(perfluoropropan-2-yl)phenylcarbamate). The method provided by the invention avoids dangerous processes such as catalytic hydrogenation and shortens reaction steps; and the preparation method of the pyridylquinazoline provided by the invention has low costs and simple and safe process operation.

Description

technical field [0001] The invention relates to a preparation method of pyridinequinazoline. Background technique [0002] Pyridine quinazoline is a new type of quinazoline insecticide, which is effective against stink bugs and has excellent effects on aphids, whiteflies, mealybugs, leafhoppers and thrips. Molecular formula: C 19 h 15 f 7 N 4 o 2 , molecular weight: 464.11, molecular structure formula: [0003] [0004] Its content and yield directly affect the production cost and use cost of this type of high-efficiency and low-toxicity insecticide. The currently reported methods mainly include the following. [0005] EP1097932 discloses a seven-step reaction synthesis of pyridinequine with 2-nitro-5-heptafluoroisopropylbenzaldehyde, methyl nitrile formate, N,N-carbonyldiimidazole, acetic anhydride, and 3-cyanopyridine. The oxazoline method. The synthesis involves two-step catalytic hydrogenation reaction, one-step high-pressure reaction, and the high-pressure r...

Claims

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Application Information

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IPC IPC(8): C07D401/12
Inventor 刘鹏王宇胡志彬杨彬
Owner 湖南速博生物技术有限公司
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