Process for chemical synthesis of 2-(cyanomethyl) thio acetyl chloride

A technology of cyanomethylthioacetyl and cyanomethylthio, which is applied in the field of chemical synthesis of 2-cyanomethylthioacetyl chloride, can solve the problems of potential safety hazards, environmental pollution and high cost, and achieves a reduction in dosage, The effect of reducing production costs and reducing the amount of three wastes

Inactive Publication Date: 2007-04-04
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] In order to solve the deficiencies in the prior art that the chemical synthesis of 2-cyanomethylthioacetyl chloride is easy to cause environmental pollution, has potential safety hazards, high cost, and low yield, the invention provides a safe and reliable production method with less pollution and mild conditions. , the chemical synthesis method of 2-cyanomethylthioacetyl chloride with high reaction yield and low cost

Method used

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  • Process for chemical synthesis of 2-(cyanomethyl) thio acetyl chloride
  • Process for chemical synthesis of 2-(cyanomethyl) thio acetyl chloride
  • Process for chemical synthesis of 2-(cyanomethyl) thio acetyl chloride

Examples

Experimental program
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Effect test

Embodiment 1

[0039] The feeding molar ratio is: potassium 2-cyanomethylthioacetate: bis(trichloromethyl) carbonate: catalyst tetrabutylurea=1: 0.35: 0.001, wherein potassium 2-cyanomethylthioacetate (C 4 h 4 NKO 2 S) 8.45g, two (trichloromethyl) carbonate (C 3 o 3 Cl 6 )5.2g, tetrabutylurea (C 17 h 36 N 2 (2) 0.02g, organic solvent dichloromethane 126.75g, consumption is 15 times of 2-cyanomethylthioacetic acid potassium.

[0040] In a 150 ml three-necked flask equipped with a thermometer, a reflux condenser, a drying tube, a constant pressure dropping funnel, and a mechanical stirrer, add potassium 2-cyanomethylthioacetate and an organic solvent, start stirring, and cool in an ice-salt bath to - 5°C, then, bis(trichloromethyl)carbonate and catalyst tetrabutylurea were added under ice-salt bath cooling. After the addition is complete, continue to stir for 2 minutes while cooling in the ice-salt bath, then remove the ice-salt bath, slowly raise the temperature to 55-60°C, and stir t...

Embodiment 2

[0042] The molar ratio of feeding is: 2-potassium cyanomethylthioacetate: bis(trichloromethyl) carbonate: catalyst tetrabutylurea=1: 0.5: 0.005, wherein 10.1 g of potassium 2-cyanomethylthioacetate, Bis(trichloromethyl)carbonate 8.9g, tetrabutyl urea 0.08g, organic solvent is 181.8g of dichloromethane, the consumption is 18 times of potassium 2-cyanomethylthioacetate.

[0043] In a 150 ml three-necked flask equipped with a thermometer, a reflux condenser, a drying tube, a constant pressure dropping funnel, and mechanical stirring, add 2-cyanomethylthioacetic acid potassium and dichloromethane, start stirring, and cool in an ice-salt bath to -5°C, then, bis(trichloromethyl)carbonate and tetrabutylurea were added under ice-salt bath cooling. After the addition is complete, continue stirring for 3 minutes while cooling in the ice-salt bath, then remove the ice-salt bath, slowly heat up to 55-60°C, and stir and react at 55-60°C for 12 hours. After the reaction was over, the solve...

Embodiment 3

[0045]The feeding molar ratio is: potassium 2-cyanomethylthioacetate: bis(trichloromethyl) carbonate: catalyst N, N'-dimethylimidazolidinone=1:0.5:0.005, wherein 2-cyanomethyl Potassium thioglycolate 8.45g, bis(trichloromethyl)carbonate 7.4g, N,N'-dimethylimidazolidinone (C 4 h 10 N 2 (0) 0.03g, organic solvent is tetrahydrofuran 143.65g, and consumption is 17 times of 2-cyanomethylthioacetic acid potassium.

[0046] In a 150 ml three-neck flask equipped with a thermometer, reflux condenser, drying tube, constant pressure dropping funnel and mechanical stirring, add potassium 2-cyanomethylthioacetate and tetrahydrofuran, start stirring, and cool to -5 in an ice-salt bath. °C, then, bis(trichloromethyl)carbonate and N,N'-dimethylimidazolidinone were added under ice-salt bath cooling. After the addition is complete, continue to stir for 2 minutes under ice-salt bath cooling, then remove the ice-salt bath, slowly heat up to 55-60°C, and stir and react at 55-60°C for 12 hours. ...

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Abstract

A method for preparing 2-[(cyanomethyl)thio]acetyl chloride, taking 2-[(cyanomethyl)thio]acetic acid potassium salt and bis(trichloro methyl)carbonate as stock, putting them into organic dissolvent for reaction under the effect of catalyst for 8-16 hours, the temperature is -5~60 DEG C, separating and purifying to get the product.The consumption of chlorizating agent in said chemosynthesis method reduces greatly for the use of bis(trichloro methyl)carbonate, which can reduces the production cost and eliminates the potential safety hazard from the preparing source, and considerably decreases the yield of three wastes and increases the yield of products and promotes the quality as well; the dissolvent can be recovered which decreases pollution and production cost.

Description

(1) Technical field [0001] The invention relates to a chemical synthesis method of 2-cyanomethylthioacetyl chloride. (2) Background technology [0002] 2-cyanomethylthioacetyl chloride is mainly used as an intermediate in the synthesis of thiocyanate series cephalosporins. In the prior art, the chemical synthesis of 2-cyanomethylthioacetyl chloride is mainly obtained by reacting 2-cyanomethylthioacetic acid potassium and oxalyl chloride as raw materials in benzene, causing larger environmental pollution on the one hand, Increase production cost, on the other hand bring very big potential safety hazard to production, and existing synthetic method yield is low (less than 70%), and purity is less than 96%. For example: US3944546, US 3855212, US 3932396, US 3932397, US 4111978, US4139618, etc.; also use 2-cyanomethylthioacetic acid to react with thionyl chloride, phosphorus oxychloride, etc. to synthesize 2-cyanomethylthioethyl The method of acyl chloride, but this kind of met...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C323/25C07C323/52C07C319/20
Inventor 苏为科李永曙李振华
Owner ZHEJIANG UNIV OF TECH
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