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Process method for synthesizing thioamide

A technology for synthesizing thioamides and thioamides, applied in organic chemistry and other directions, can solve the problems of difficult industrialization, phosphorus waste water, expensive reagents, etc., and achieve the effects of improved effective utilization, mild reaction conditions, and enhanced safety.

Inactive Publication Date: 2017-07-07
SUZHOU HOMESUN PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] 3. Use hydrogen sulfide gas, organic amine and nitrile group-containing compound to carry out addition reaction in autoclave or under normal pressure to produce thioamide, wherein the pressurized reaction yield is 85%. Adopting this method also requires the use of pressure Reactor and highly toxic hydrogen sulfide gas, there is a high safety risk
[0016] 6. Adopting the aromatic derivatives of phosphorus pentasulfide, called Laweson reagent, reacts with amides to generate thioamides. This method also has the problems of expensive reagents, a large amount of highly toxic hydrogen sulfide waste gas that cannot be utilized, and a large amount of phosphorus-containing waste gas. Wastewater, malodorous sulfur by-products
[0017] 7. It has been reported abroad that thioamides are synthesized in one step by reacting thioacetic acid with fatty nitriles or aromatic nitriles at 80°C under the action of calcium hydride, with a yield of 76-95%. This method uses expensive and dangerous hydrogenation reagents and thioacetic acid. Difficult to industrialize (Synlett, 2009, (14): 2338)

Method used

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  • Process method for synthesizing thioamide
  • Process method for synthesizing thioamide
  • Process method for synthesizing thioamide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Add 11g of sodium hydrosulfide, 6g of p-hydroxybenzonitrile, 6.9mL of triethylamine, and 40mL of ethanol into a 100mL three-necked flask, control the temperature in an ice bath to 5-10°C, add 27.5g of triethylamine hydrochloride solid in batches, add After raising the temperature to 50° C., keeping the temperature under stirring for 12 hours, TLC monitored the reaction to be complete, and liquid phase monitoring showed that the conversion rate was above 95%, and the final yield was 92%. After the reaction, the ethanol recovered by distillation can be used directly, adding 40 mL of ethanol to the residue of distillation to make a slurry at 50°C, stirring for 0.5 hours, and filtering to obtain the by-product sodium chloride solid salt with higher purity, which can be sold for processing. The ethanol filtrate was concentrated to dryness, and the residue was slurried by adding 25 mL of water, filtered, and dried to obtain 7.32 g of yellowish solid. The liquid phase content i...

Embodiment 2

[0046] Add 16.8g of sodium hydrosulfide, 6g of p-hydroxybenzonitrile, 1.7mL of dimethylamine, and 40mL of methanol into a 100mL three-necked flask, control the temperature in an ice bath at -5~0℃, add 28.7g of isopropylamine hydrochloride solid in batches, After the addition, the temperature was raised to 30°C, and the temperature was kept under stirring for 11 hours. TLC monitored the reaction to be complete, and liquid phase monitoring showed that the conversion rate was above 95%, and the final yield was 92%. After the reaction, the methanol recovered by distillation can be directly used, and the residue of distillation is added with 40mL methanol to make a slurry at 50°C, stirred for 0.5 hours, and filtered to obtain the by-product sodium chloride solid salt with higher purity, which can be sold for processing. The methanol filtrate was concentrated to dryness, and the residue was slurried by adding 25 mL of water, filtered, and dried to obtain 6.7 g of ochre solid. The liq...

Embodiment 3

[0048] Add 31.2g of sodium sulfide, 6g of p-hydroxybenzonitrile, 12.8mL of isopropylamine, and 50mL of isopropanol into a 100mL three-necked flask, control the temperature in an ice bath at -2~2℃, and add 42g of dimethylamine acetate solid in batches. After adding, raise the temperature to 10°C, keep it for 10 hours under stirring, and filter with suction to obtain the by-product sodium acetate solid salt with higher purity, which can be sold for processing. The filtrate was distilled to recover the isopropanol and used directly in the next batch, the distillation residue was added with an appropriate amount of isopropyl ether to make a slurry, filtered with suction, and dried to obtain 6.7 g of an earthy yellow solid with a liquid content of 93% and a yield of 81.2%.

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Abstract

The invention discloses a method for synthesizing thioamide, which comprises the following steps: using fatty nitrile or aromatic nitrile as raw material, using alkali metal sulfide or ammonium sulfide and amine salt or ammonium sulfide to synthesize sulfur in one step in a certain solvent Substituting amide compounds, the synthesis method of the invention has high safety, less environmental pollution, avoids the use of expensive raw materials, and is economical and environmentally friendly.

Description

Technical field [0001] The invention relates to the field of chemical synthesis, in particular to a new method for synthesizing thioamide. Background technique [0002] Thioamide is a sulfur-containing compound in which the oxygen atom in the amide molecule is replaced by a sulfur atom. Its chemical structure is [0003] [0004] In the formula, R can be an aromatic group or an aliphatic hydrocarbon, and the hydrogen atom on the nitrogen atom can be replaced by an appropriate group. [0005] Aromatic and aliphatic thioamides are widely used and are often used as intermediates in the synthesis of many products. Thiophene compounds can be synthesized with thioamides. For example, the important intermediate of febuxostat, 2-(4-hydroxyphenyl)-4-methyl-5-thiazolecarboxylic acid ethyl ester, is derived from 4-hydroxythiobenzamide synthesis. Many thiophene compounds are important intermediates in pharmaceuticals. [0006] The methods for synthesizing thioamide in the prior art mainly inc...

Claims

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Application Information

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IPC IPC(8): C07C327/42C07C327/48
CPCC07C327/42C07C327/48
Inventor 翟金星樊超
Owner SUZHOU HOMESUN PHARMA
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