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Preparation method of chlorhexidine compound

A kind of technology of diclofenac and compound, which is applied in the field of preparation of antibacterial agent-diclofenac compound, and can solve the problems affecting the industrial application of diclofenac, high price of solvent nitrobenzene, side reaction It is difficult to control and other problems, and achieves the effect of good industrial application prospects, simplified post-processing process and short reaction time.

Inactive Publication Date: 2013-03-27
GANSU RES INSTION OF CHEM IND GRICI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In this method, the price of solvent nitrobenzene is relatively expensive, and the pollution is high, the toxic and side effects are large, the total yield is low, and the side reactions are difficult to control, etc., thus affecting the industrial application of chlorhexidine

Method used

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  • Preparation method of chlorhexidine compound
  • Preparation method of chlorhexidine compound
  • Preparation method of chlorhexidine compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] (1) Preparation of hexylene-dicyanoguanidine

[0021] Weigh hexamethylenediamine hydrochloride (9.45g, 0.05mol) and sodium dicyandiamide (8.90g, 0.1mol) into a 250ml three-necked flask, add 200ml of n-butanol, heat to 130°C, and reflux under magnetic stirring 2h; Distill the reaction solution under reduced pressure to remove n-butanol, then add water, stir and wash 3 times, and filter to obtain a white solid; the white solid is vacuum-dried at 0.06MPa and 60°C to obtain pure 1,6-dicyanoguanidine Hexane compounds. The weighing calculation yield was 96%.

[0022] Product characterization data: IR(neat)ν:3447,3146,2942,2867,2179,1660,1620,1541,1477,1432,1378,

[0023] 1327,1124,942cm -1 .Anal.calcdforC 10 h 18 N 8 .C47.98,H7.25,N44.77.foundC48.01,H7.23,N44.76. 1 HNMR (400MHz, DMSO) δ :1.23-1.40(m,8H,-CH 2 -),2.99-3.37(m,4H,-CH 2 -N),6.56-7.26(NH,6H).ESI + -MS(35eV,m / Z):251[M+H] + .

[0024] Its structural formula is:

[0025]

[0026] (2) Preparation of ch...

Embodiment 2

[0034] (1) Preparation of hexylene-dicyanoguanidine: same as Example 1.

[0035] (2) Preparation of chlorhexidine:

[0036] Weigh hexylene-dicyanoguanidine (2.5g, 0.01mol) and p-chloroaniline hydrochloride (3.9g, 0.024mol) into a 100ml three-neck flask, add solvent ethylene glycol ether; magnetic stirring, 135°C Condensate under reflux for 3 hours to obtain a reaction liquid; stand still, and obtain a white solid by suction filtration; take out the solid, wash it with water, and obtain a crude product by suction filtration; purify to obtain a pure chlorhexidine compound. The calculated yield by weighing was 78.1%.

[0037] The characterization of the product is the same as in Example 1.

Embodiment 3

[0039] (1) Preparation of hexylene-dicyanoguanidine: same as Example 1.

[0040] (2) Preparation of chlorhexidine:

[0041] Weigh hexylene-dicyanoguanidine (2.5g, 0.01mol), p-chloroaniline hydrochloride (2.8g, 0.016mol), add to a 100ml three-necked flask, add solvent ethylene glycol ether, magnetically stir, 135°C Condensate under reflux for 3 hours to obtain a reaction liquid; stand still, and obtain a white solid by suction filtration; take out the solid and wash it with water, and obtain a crude product by suction filtration; purify to obtain a pure chlorhexidine compound. The calculated yield by weighing was 74.8%.

[0042] The characterization of the product is the same as in Example 1.

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Abstract

The invention discloses a preparation method of chlorhexidine compound and belongs to the field of organic chemical synthesis. The preparation method comprises the following steps: carrying out a heating reflux reaction on hexamethylene-dicyanoguanidine and chloroaniline hydrochloride as raw materials and glycol ether or normal butanol as a solvent to directly obtain a target compound in a single step. The preparation method is simple in process, mild in reaction condition, short in reaction time, rapid and efficient; as the glycol ether or normal butanol is used as the solvent, the influence of the toxic or side effect of the solvent on a human body is reduced, meanwhile the environmental pollution is reduced; and as a catalyst is not used in the synthesis process, an aftertreatment process is simplified, the synthetic comprehensive cost is effectively reduced, the yield of a final product can reach as high as 84.7%, the purity of the final product can reach as high as 97%, thus the preparation method has a better industrial application prospect.

Description

technical field [0001] The invention belongs to the field of organic synthesis chemistry, and relates to a preparation method of an antibacterial agent-chlorhexidine compound. Background technique [0002] Chlorhexidine hydrochloride, also known as chlorhexidine hydrochloride, has quite strong broad-spectrum antibacterial and bactericidal effects. It is a better bactericidal disinfectant, and its antibacterial effect on Gram-positive and negative bacteria Such disinfectants are strong and effective even in the presence of serum, blood, etc. It is widely used in the fields of oral anti-inflammation, inhibition of dental plaque formation, treatment of acne and disinfection of abdominal cavity and intestinal mucosa during surgery. [0003] The molecular formula of chlorhexidine is: C 22 h 30 C l2 N 10 2HCl; the chemical structural formula is: [0004] [0005] At present, the synthesis of chlorhexidine is generally prepared by reacting p-chloroaniline hydrochloride and...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C279/26C07C277/08
Inventor 刘国华耿来红张鹏云刘茵霍利春
Owner GANSU RES INSTION OF CHEM IND GRICI
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