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Method for synthesizing 2-(3-cyano-4- isobutoxy phenyl)-4-methyl-carboxylate

A technology of isobutoxyphenyl thioformamide and isobutoxyphenyl, which is applied in the field of medicine, can solve the problems of unsuitability for industrial production, difficult availability of raw materials, and high production costs, and achieve low cost and easy availability of raw materials , the effect of less waste

Active Publication Date: 2009-08-05
SHENYANG PHARMA UNIVERSITY +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The technical problem to be solved in the present invention is that the existing 2-(3-cyano-4-isobutoxyphenyl)-4-methyl-5-thiazole formic acid synthesis process is not suitable for industrialized production, high production cost, and safe Poor performance, and the raw materials are not easy to obtain and other problems

Method used

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  • Method for synthesizing 2-(3-cyano-4- isobutoxy phenyl)-4-methyl-carboxylate
  • Method for synthesizing 2-(3-cyano-4- isobutoxy phenyl)-4-methyl-carboxylate
  • Method for synthesizing 2-(3-cyano-4- isobutoxy phenyl)-4-methyl-carboxylate

Examples

Experimental program
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Effect test

Embodiment 1

[0030] 1) 3-iodo-4-hydroxybenzonitrile

[0031] In a 250ml three-necked bottle, add 16.7g of potassium iodide, 21.3g of iodine, 86ml of water, and 14ml of concentrated ammonia water, stir mechanically at room temperature, add 10.0g of 4-hydroxybenzonitrile after dissolution, and react for 7 hours at room temperature. After the reaction was completed, the pH was adjusted to 1 with concentrated hydrochloric acid in an ice bath, and after standing for 1 hour, it was suction filtered, washed with water, and dried to obtain 18.8 g of a khaki solid, yield: 91.5%. ESI-MS m / z: 268[M+Na] + , 244[M-H] -

[0032] 2) 3-iodo-4-isobutoxybenzonitrile

[0033] In a 250ml round bottom flask, add 18.8g of 3-iodo-4-hydroxybenzonitrile, 15.9g of anhydrous potassium carbonate, 100ml of DMF, 3ml of PEG4003ml, stir at 60°C for 15min, then add 26.1g of bromoisobutane g, continue the reaction, raise the temperature to 80°C after 6h, and distill under reduced pressure for 1-2h (distill the excess i...

Embodiment 2

[0043] 1) 3-iodo-4-hydroxybenzonitrile

[0044] In a 250ml three-necked bottle, add 33.5g potassium iodide, 43.7g iodine, 172ml water, and 28ml concentrated ammonia water, stir mechanically at room temperature, add 20.0g 4-hydroxybenzonitrile after dissolution, and react for 7 hours at room temperature. After the reaction was completed, the pH was adjusted to 1 with concentrated hydrochloric acid in an ice bath, and after standing for 1 hour, it was suction filtered, washed with water, and dried to obtain 40.0 g of a khaki solid, yield: 97.1%.

[0045] 2) 3-iodo-4-isobutoxybenzonitrile

[0046] In a 250ml round bottom flask, add 40.0g of 3-iodo-4-hydroxybenzonitrile, 33.7g of anhydrous potassium carbonate, 200ml of DMF, 6ml of PEG, stir at 60°C for 15min, then add 55.5g of bromoisobutane g, to continue the reaction, raise the temperature to 80°C after 6h, and distill under reduced pressure for 1-2h (distill the excess isobutane bromide). Suction filtration, wash the filter c...

Embodiment 3

[0056] 1) 3-iodo-4-hydroxybenzonitrile

[0057] In a 1000ml three-necked bottle, add 100g of potassium iodide, 128g of iodine, 516ml of water, and 86ml of concentrated ammonia water, stir mechanically at room temperature, add 60.0g of 4-hydroxybenzonitrile after dissolution, and react for 7 hours at room temperature. After the reaction was completed, the pH was adjusted to 1 with concentrated hydrochloric acid in an ice bath, and after standing for 1 h, the mixture was suction filtered, washed with water, and dried to obtain 116.0 g of a khaki solid, yield: 94.3%.

[0058] 2) 3-iodo-4-isobutoxybenzonitrile

[0059]In a 1000ml round bottom flask, add 116.0g of 3-iodo-4-hydroxybenzonitrile, 98.0g of anhydrous potassium carbonate, 500ml of DMF, 10ml of PEG400, stir at 60°C for 15min, then add bromoisobutyl 160.1 g of alkanes continued to react, and after 6 hours, the temperature was raised to 80° C., and vacuum distillation was performed for 1 to 2 hours (excess bromoisobutane w...

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Abstract

The invention belongs to the technical field of medicine, and relates to a method for synthesizing 2-(3-cyano-4-isobutoxy phenyl)-4-methyl-5-thiazole formic acid. The method comprises that: 4-hydroxyl cyanobenzene is used as a raw material, and subjected to iodination, hydrocarbylation and cyanation to obtain an intermediate of 4-isobutoxy-1,3-benzene dinitrile, the intermediate reacts with sodium bisulfide and anhydrous magnesium chloride to obtain a key intermediate of 3-cyano-4-isobutoxy phenyl thioformamide, and the 3-cyano group-4-isobutoxy phenyl thioformamide is subjected to cyclization and hydrolysis reaction to obtain the 2-(3-cyano-4-isobutoxy phenyl)-4-methyl-5-thiazole formic acid. The method has the advantages of easily obtained materials, simple and convenient operation, high yield, low cost and suitability for industrialized production.

Description

technical field [0001] The invention belongs to the technical field of medicine, relates to a synthesis method of 2-(3-cyano-4-isobutoxyphenyl)-4-methyl-5-thiazolecarboxylic acid, and also relates to its intermediate 4-isobutyl Synthetic method of oxy-1,3-phthalonitrile and 3-cyano-4-isobutoxybenzenethiocarboxamide. Background technique [0002] Gout is a group of heterogeneous metabolic diseases caused by long-term purine metabolic disorders and / or decreased uric acid excretion. Gout is the second most common metabolic disease in humans after diabetes. The clinical features of gout are hyperuricemia, recurrent acute arthritis, tophi deposition, tophi chronic arthritis and joint deformities, chronic interstitial nephritis and nephrolithiasis caused by kidney involvement. Often complicated by cardiovascular and cerebrovascular diseases and life-threatening. The prerequisite for the onset of gout is hyperuricemia. Hyperuricemia refers to the uric acid content in serum at 37...

Claims

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Application Information

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IPC IPC(8): C07D277/56A61P19/06
Inventor 王绍杰陈家润薛明星
Owner SHENYANG PHARMA UNIVERSITY
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