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Method for preparing 3-sulfydryl coumarin

A technology of mercaptocoumarin and thioglycolic acid, applied in the direction of organic chemistry, can solve the problems of low yield, complicated post-processing, long reaction time, etc., and achieve the effects of low reaction temperature, low production cost and simple process

Active Publication Date: 2016-01-20
江西扬帆新材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0017] The above several synthetic methods have the disadvantages of low yield, long reaction time and complex post-treatment.

Method used

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  • Method for preparing 3-sulfydryl coumarin
  • Method for preparing 3-sulfydryl coumarin
  • Method for preparing 3-sulfydryl coumarin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] The preparation method of embodiment 1,3-mercaptocoumarin:

[0029] Under ice-bath condition, in the there-necked flask of 100ml, add 40.0g mass concentration and be the sodium hydroxide aqueous solution (0.30mol) of 30%, again in N 2 Add 11.0 g (0.12 mol) of thioglycolic acid under the protection of . After uniformly stirring for a period of time (about 20 to 30 minutes), add 14.0 g (0.10 mol) of o-chlorobenzaldehyde to the kettle liquid, raise the temperature to reflux temperature (T=108° C.), and reflux at this temperature for 4 hours. The reaction pressure is normal pressure. After the reaction, add concentrated hydrochloric acid (36.5wt%) to the still liquid until the still liquid is weakly acidic (i.e., adjust pH = 3 to 4), filter and dry (dry at 80°C for 10 h) to obtain 16.3 g of a yellow solid, which is a crude product 3-Mercaptocoumarin. The crude product was recrystallized with absolute ethanol (20ml), and after vacuum filtration, washing (washing with 30ml...

Embodiment 2

[0030] The preparation method of embodiment 2,3-mercaptocoumarin:

[0031] Under ice-bath condition, in the there-necked flask of 250ml, add 140.0g mass concentration and be 25% sodium hydroxide aqueous solution (0.875mol), again in N 2 26.7 g (0.29 mol) of thioglycolic acid were added under the protection of . After uniform stirring for a period of time, 35.1g (0.25mol) of o-chlorobenzaldehyde was added to the kettle liquid, and the temperature was raised to reflux temperature (T=106°C), and reflux reaction was carried out at this temperature for 4.5h, and the reaction pressure was normal pressure. After the reaction was completed, concentrated hydrochloric acid (36.5 wt %) was added to the still liquid until the still liquid was weakly acidic, and 41.2 g of a yellow solid was obtained by filtration and drying, which was the crude product 3-mercaptocoumarin. The crude product was recrystallized with absolute ethanol, and after vacuum filtration, washing and drying, 39.3 g of...

Embodiment 3

[0032] The preparation method of embodiment 3,3-mercaptocoumarin:

[0033] Under ice-bath condition, in the there-necked flask of 500ml, add 195.0g mass concentration and be 40% sodium hydroxide aqueous solution (1.95mol), again in N 2 71.9 g (0.78 mol) of thioglycolic acid were added under the protection of . After uniform stirring for a period of time, 84.3g (0.60mol) of o-chlorobenzaldehyde was added to the kettle liquid, and the temperature was raised to reflux temperature (T=112°C), and reflux reaction was carried out at this temperature for 3.5h, and the reaction pressure was normal pressure. After the reaction was finished, concentrated hydrochloric acid (36.5 wt %) was added to the still liquid until the still liquid was weakly acidic, and 98.4 g of a yellow solid was obtained by filtration and drying, which was the crude product 3-mercaptocoumarin. The crude product was recrystallized with absolute ethanol, and after vacuum filtration, washing and drying, 92.1 g of w...

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Abstract

The invention discloses a method for preparing 3-sulfydryl coumarin. The method comprises the following steps: in an alkali liquid, enabling o-chlorobenzaldehyde and mercaptoacetic acid as raw materials to react at 85-115 DEGC for 3-6 hours, wherein the mole ratio of o-chlorobenzaldehyde to mercaptoacetic acid is 1:(1.1-1.3), and the amount of the alkali is 2.5-3.5 mole times of mercaptoacetic acid; after the reaction, adding concentrated hydrochloric acid to acidify till the pH value of the reaction product (kettle liquid) is 3-4, filtering, and drying, thereby obtaining a crude product 3-sulfydryl coumarin; re-crystallizing the crude product 3-sulfydryl coumarin by using absolute ethyl alcohol, performing vacuum suction filtration, washing, and drying, thereby obtaining 3-sulfydryl coumarin. The method for preparing 3-sulfydryl coumarin has the characteristics of wide raw material source, low production cost, simple process, low reaction temperature, high yield, applicability to scale production, and the like.

Description

technical field [0001] The invention relates to a method for preparing 3-mercaptocoumarin from o-chlorobenzaldehyde and thioglycolic acid as raw materials. Background technique [0002] [0003] 3-Mercaptocoumarin, whose structural formula is shown as S-1, is widely used in the fields of antibacterial and rodenticide, and is also an important intermediate for the synthesis of benzothiophene 2-carboxylic acid. [0004] There are the following several synthetic methods of 3-mercaptocoumarin reported in the literature at present: [0005] (1) Using 2-methyl-2-phenyl-1,3-oxathiolan-5-one and salicylaldehyde as raw materials [0006] LalDharS. et al. (LalDharS.Yadav, SantoshSinghandVijaiK.Rai.Catalyst-free, stepandpoteconomic, efficientmercaptoacetylativecyclisationinH2O:synthesisof3-mercaptocoumarins.GreenChemistry, 2009,11,878-882) with water as solvent and catalyst, with 2-methyl-2phenyl- 1,3-Oxathiolane-5-one and salicylaldehyde were used as raw materials, and refluxed f...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/12
CPCC07D311/12
Inventor 樊彬高武成吕雪皓余立志陈育亮
Owner 江西扬帆新材料有限公司
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