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Method for preparing thio-iso-butanamide

A technology of thioisobutyramide and isobutyramide, applied in the field of medicine and chemical industry, can solve the problems of low yield, difficult separation of products and raw materials, etc., and achieve the effect of stable reaction

Active Publication Date: 2009-10-21
南通森萱药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The product is difficult to separate from the raw material, and the yield is low, about 80%

Method used

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  • Method for preparing thio-iso-butanamide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] In 600ml of ethyl acetate, add 12g of phosphorus pentasulfide, add 5.8g of anhydrous sodium carbonate in batches, and stir at 20-25°C for 30mins. After the solid was completely dissolved, 20 g of isobutyramide was added in batches, and the reactant was stirred at 25° C. for 5 hrs. The reaction mixture was filtered, the solution was concentrated, and distilled under reduced pressure. The yield was 115-118° C. / 5mmHg fraction to obtain a light yellow oily liquid, and 22.5 g of thioisobutyramide was obtained. The yield was 95.00%, and the GC content: 99.2%.

Embodiment 2

[0022] In 400ml tetrahydrofuran, add 8g phosphorus pentasulfide, add 9.35g anhydrous sodium carbonate in batches, T=23-25°C, stir for 25mim. 15.2 g of isobutyramide was added in batches. The reactant was stirred at 20-25° C. for 5 hrs. Tetrahydrofuran was recovered under reduced pressure, 50ml of water was added, the pH was adjusted to 7.5 with 5% aqueous sodium carbonate solution, extracted three times with 50mlx3 ethyl acetate, the organic layers were combined and washed with 100ml of saturated brine. Dry over anhydrous sodium sulfate, filter, recover ethyl acetate under reduced pressure, and distill the residue under reduced pressure, collect fractions at 112-118°C / 4mmHg to obtain yellow oily liquid, weight 16.2g, yield 91.2%.

Embodiment 3

[0024] Add 12.5g of phosphorus pentasulfide to 400ml of methyl tert-butyl ether, add 7.6g of anhydrous potassium carbonate in batches, and stir at 20-25°C for 30mins. 20.2 g of isobutyramide was added in batches. The reaction was stirred at 25-30°C for 5.5 hrs. The reactant was filtered, the solution was concentrated, the residue was distilled under reduced pressure, and fractions at 116-120°C / 5mmHg were collected to obtain a pale yellow oily liquid. The weight is 21.8g, the yield is 92%, and the GC content is 99.1%.

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Abstract

The invention relates to the field of medicine and chemical industry, in particular to a preparation method of thioisobutyramide. In the present invention, isobutyramide is reacted with phosphorus pentasulfide under normal temperature and normal pressure under alkaline conditions, and the thioisobutyramide is synthesized in high yield, the yield is ≥90%, and the content is ≥99%.

Description

technical field [0001] The invention relates to the field of medicine and chemical industry, in particular to a preparation method of thioisobutyramide. Background technique [0002] 2-isopropyl-4-(((N-methyl)amino)methyl)thiazole hydrochloride is an important intermediate of the anti-AIDS drug ritonavir. The synthetic route of the compound disclosed in WO2006 / 090270A1 comprises the following steps: [0003] 1. Use isobutyramide and phosphorus pentasulfide to react in an organic solvent to generate thioisobutyramide. [0004] 2. Cyclization reaction between thioisobutyramide and dichloroacetone to generate 2-isopropyl-4-chloromethylthiazole. [0005] 3. 2-isopropyl-4-chloromethylthiazole reacts with methylamine at room temperature to generate 2-isopropyl-4-(((N-methyl)amino)methyl)thiazole. [0006] 4. Salt formation of 2-isopropyl-4-(((N-methyl)amino)methyl)thiazole with hydrochloric acid, and crystallization in an organic solvent to obtain the target product. [0007] ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C327/42
Inventor 童贞明马峰
Owner 南通森萱药业有限公司
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