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Preparation method of 1-chloroethyl cyclohexyl propyl carbonate

A technology of cyclohexyl propyl carbonate and chloroethyl, applied in the field of preparation of 1-chloroethyl cyclohexyl propyl carbonate, can solve the problems of toxic gas leakage, high risk, uneconomical, etc. Small, low-cost, easy-to-control effects

Active Publication Date: 2015-04-08
扬州三友合成化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Method 1 uses highly toxic gases phosgene and acetaldehyde, so the process control requirements are relatively strict, and it is easy to cause toxic gas leakage, which is highly dangerous; method 2 will generate sulfur dioxide waste gas during the synthesis process, and because of product
[0009] , resulting in a product yield of only 40-50%, so it is neither environmentally friendly nor economical

Method used

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  • Preparation method of 1-chloroethyl cyclohexyl propyl carbonate
  • Preparation method of 1-chloroethyl cyclohexyl propyl carbonate
  • Preparation method of 1-chloroethyl cyclohexyl propyl carbonate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] (1) In a 1000ml reaction bottle, put 198g of trichloromethyl chloroformate, start stirring, when the temperature of trichloromethyl chloroformate drops to -10~0℃, add 2g of triethylamine, dropwise add 88g of paraldehyde , the dropping process takes 4 hours. After the dropping is completed, continue to stir the reaction for 2h, then add 206g of triethylamine, and add 200g of cyclohexanol dropwise after the temperature after mixing is 19°C. After the dropwise addition, continue to stir and react for 3h .

[0028] After the reaction was finished, 100 g of water was added, and the organic phase was separated to be the crude product of 1-chloroethylcyclohexylpropyl carbonate.

[0029] (2) Put the crude product of 1-chloroethylcyclohexylpropyl carbonate into the rectification reaction bottle, control the temperature in the bottle below 130°C, and conduct vacuum distillation to obtain 1-chloroethylcyclohexylpropyl Carbonic acid ester 380g, yield is 92%, and purity is greater ...

Embodiment 2

[0031] (1) In a 1000ml reaction bottle, put 238g of trichloromethyl chloroformate, start stirring, cool down to -10~0℃, add 2.4g of pyridine, dropwise add 106g of paraldehyde, the dropwise addition process takes 6 hours, dropwise After completion, continue stirring for 2 hours, add 247 g of pyridine, and add 240 g of cyclohexanol dropwise after the temperature after mixing is below 20°C, and continue stirring for 3 hours after the dropwise addition is complete.

[0032] After the reaction was completed, 120 g of water was added, and the organic phase was separated to be crude 1-chloroethylcyclohexylpropyl carbonate.

[0033] (2) Put the crude product of 1-chloroethylcyclohexylpropyl carbonate into the rectification reaction bottle, control the temperature in the bottle below 130°C, and conduct vacuum distillation to obtain 1-chloroethylcyclohexyl Propyl carbonate 461g, the yield is 93%, and the purity is greater than 99.5%.

Embodiment 3

[0035] (1) In a 1000ml reaction bottle, put 218g of trichloromethyl chloroformate, start stirring, cool down to -10~0℃, add 2.4g of N,N-dimethylaniline, dropwise add 116.6g of paraldehyde, drop The process takes 6 hours. After the dropwise addition, continue to stir for 2 hours, add 272g of N,N-dimethylaniline, after the temperature after mixing is below 20°C, add 220g of cyclohexanol dropwise, after the dropwise addition, continue to stir for 3h .

[0036] After the reaction was completed, 110 g of water was added, and the organic phase was separated to be crude 1-chloroethylcyclohexylpropyl carbonate.

[0037] (2) Put the crude product of 1-chloroethylcyclohexylpropyl carbonate into the rectification reaction bottle, control the temperature in the bottle below 130°C, and conduct vacuum distillation to obtain 1-chloroethylcyclohexyl Propyl carbonate 420g, the yield is 92.5%, and the purity is greater than 99.5%.

[0038] In the present invention, when step 1) uses one of tr...

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Abstract

The invention relates to a preparation method of 1-chloroethyl cyclohexyl propyl carbonate and belongs to the field of chemicals. The preparation method of 1-chloroethyl cyclohexyl propyl carbonate comprises the following steps of: adding triethylamine or pyridine or N,N-dimethylaniline into trichloromethyl chloroformate at the temperature between 10 DEG C below zero and 0 DEG C, and dropwise adding paraldehyde to carry out reaction; adding triethylamine or pyridine or N,N-dimethylaniline after reaction, dropwise adding cyclohexanol under the condition that the temperature in a reactor is below 20 DEG C, and stirring to carry out reaction; taking a product of reaction, washing with water, and distilling by reducing pressure to obtain an organic phase which is 1-chloroethyl cyclohexyl propyl carbonate. The synthesized 1-chloroethyl cyclohexyl propyl carbonate is high in yield and purity and low in cost, and the preparation method of 1-chloroethyl cyclohexyl propyl carbonate is easy to control in the preparation process, is easy to operate, is low in risk and is particularly suitable for industrial production.

Description

technical field [0001] The invention mainly relates to the field of chemical medicines, in particular to a preparation method of 1-chloroethylcyclohexylpropyl carbonate. Background technique [0002] Chloromethyl isopropyl carbonate is an intermediate for the synthesis of candesartan cilexetil and cefotiam cilexetil. Candesartan cilexetil is a drug institution suitable for essential hypertension, mainly angiotensin lI is a comprehensive drug composed of receptor antagonist (AT) antihypertensive drugs. This drug has a long onset period, relatively good bioavailability, and strong antihypertensive effect during application. It has attracted the attention and attention of people from all walks of life at home and abroad due to its advantages of small side effects and has become the most common type of hypertension drug preparation. Cefotiam is an oral antibiotic derived from cefotiam ethyl for injection. [0003] Present 1-chloroethyl cyclohexyl propyl carbonate synthetic met...

Claims

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Application Information

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IPC IPC(8): C07C69/96C07C68/02
CPCC07C68/02C07C68/08C07C69/96
Inventor 李辉宁李明成张扬张众笑
Owner 扬州三友合成化工有限公司
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