Method used for synthesizing 1,5,7-Triazabicyclo[4.4.0]dec-5-ene (TBD) via phase-transfer catalysis

A technology of phase transfer catalysis and phase transfer catalyst, applied in organic chemistry and other directions, can solve the problems of slow reaction rate, high reaction temperature, difficult product TBD purification, etc., and achieve the effect of short time and low reaction temperature.

Active Publication Date: 2015-08-19
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage of this method is that the reaction rate is slow, the reaction temperature is high, and the product TBD is difficult to purify.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Add the aqueous solution 20mL (5mmol / mL) of GHC in the 100mL reactor that is equipped with reflux condenser and electric stirring equipment, the mesitylene solution 20mL (5.0mmol / mL) of APA, the macroporous anion exchange resin ( D201) 0.29g, reacted for 10h under the protection of argon at 80°C.

[0024] After the reaction is completed, the reaction mixture is firstly recovered by filtration for D201 resin (recovered resin is washed and dried for repeated synthesis experiments), and then the water-oil two-phase system from which the resin has been filtered is recovered by a separatory funnel for oil phase mesitylene. After the aqueous phase was rotary evaporated, a light yellow viscous liquid was obtained. The latter was extracted with 30 mL of dichloromethane. After the extract was rotary evaporated to recover the dichloromethane, the colorless oily liquid was placed in the freezer of the refrigerator at -14°C for 8 hours, and then placed at room temperature (15-25°C)...

Embodiment 2

[0026] Add 20mL (5.5mmol / mL) of GHC's aqueous solution, 20mL (5.0mmol / mL) of APA's mesitylene solution to the 100mL reaction kettle equipped with reflux condenser and electric stirring equipment, pretreated macroporous anion exchange resin (D201) 0.42g, react under argon protection at 105°C for 8h.

[0027] After the reaction is completed, the reaction mixture is firstly recovered by filtration for D201 resin (recovered resin is washed and dried for repeated synthesis experiments), and then the water-oil two-phase system from which the resin has been filtered is recovered by a separatory funnel for oil phase mesitylene. After the aqueous phase was rotary evaporated, a light yellow viscous liquid was obtained. The latter was extracted with 30 mL of dichloromethane. After the extract was rotary evaporated to recover the dichloromethane, the colorless oily liquid was placed in the freezer of the refrigerator at -14°C for 10 hours, and then placed at room temperature (15-25°C) unt...

Embodiment 3

[0029] Add 20mL (6.0mmol / mL) of GHC's aqueous solution, 20mL (5.0mmol / mL) of APA's mesitylene solution, and pretreated macroporous anion exchange resin into a 100mL reaction kettle equipped with a reflux condenser and electric stirring equipment. (D201) 0.57g, reacted under argon protection at 120°C for 9h.

[0030] After the reaction is completed, the reaction mixture is firstly recovered by filtration to recover the D201 resin (the recovered resin is washed and dried for repeated synthesis experiments), and then the oil phase mesitylene is recovered from the water-oil two-phase system from which the resin has been filtered out by a separatory funnel. After the aqueous phase was rotary evaporated, a light yellow viscous liquid was obtained. The latter was extracted with 30 mL of dichloromethane. After the extract was rotary evaporated to recover the dichloromethane, the colorless oily liquid was placed in the freezer of the refrigerator at -14°C for 12 hours, and then placed ...

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Abstract

The invention discloses a method used for synthesizing 1,5,7-Triazabicyclo[4.4.0]dec-5-ene (TBD) via phase-transfer catalysis. According to the method, bis(3-amino propyl)amine and guanidine hydrochloride are taken as raw materials, macroporous anion exchange resin is taken as a phase-transfer catalyst, and TBD (1,5,7-Triazabicyclo[4.4.0]dec-5-ene) is synthesized in a water-oil double-phase solution. Beneficial effects are that: reaction temperature is low; reaction time is short; operation is simple; and the used phase-transfer catalyst and solvent mesitylene can be recycled.

Description

technical field [0001] The invention belongs to the field of organic synthesis and relates to a new process for synthesizing organic bicyclic guanidine TBD (1,5,7-triazabicyclo[4.4.0]-dec-5-ene). Background technique [0002] 1,5,7-Triazabicyclo[4.4.0]-dec-5-ene (English abbreviation: TBD, Chinese abbreviation: bicyclic guanidine) has unique physical and chemical properties, making it suitable for use in many organic and polymerization reactions Shows excellent catalytic performance. [0003] The synthesis methods of 1,5,7-triazabicyclo[4.4.0]-dec-5-ene (TBD) mainly include: [0004] (1) The reaction preparation method of bis(3-aminopropyl)amine and carbon dichloride. The disadvantage of this method is that the raw material carbon dichloride has high toxicity and the synthesis process is relatively cumbersome. [0005] (2) Carbon disulfide instead of carbon dichlorosulfide and bis(3-aminopropyl)amine reaction preparation method. The disadvantage of this method is that ca...

Claims

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Application Information

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IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 李弘张全兴孙向前江伟黄伟李爱民
Owner NANJING UNIV
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