Preparation method of 1,4,7,10-tetraazadodecane

A technology of tetraazadodecane and dimethyl acetal, which is applied in the field of preparation of 1,4,7,10-tetraazadodecane, which can solve the problems of long production cycle, cumbersome operation steps and low product yield. Not very ideal and other problems, to achieve the effect of convenient operation and simple process

Inactive Publication Date: 2013-02-27
太仓市茜泾化工有限公司
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  • Abstract
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  • Application Information

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Problems solved by technology

Although this method improves the yield of the target, it also makes the operation steps more complicated, the production cycle becomes longer, the final product yield is still not very ideal, and the cost has not decreased.

Method used

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  • Preparation method of 1,4,7,10-tetraazadodecane

Examples

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Effect test

Embodiment 1

[0020] The preparation of embodiment 1 two imidazolines

[0021] In a four-necked flask equipped with a reflux condenser, a thermometer, a drying tube, and a stirrer, add TETA14.6g (0.1mol), N,N-dimethylformamide dimethyl acetal (95%) 25g (0.2mol ), 60ml of benzene, heated to 80°C, and continuously distilled off the methanol generated by the reaction, refluxed for 2 hours, steamed out an appropriate amount of benzene under reduced pressure, cooled, crystallized, and filtered to obtain 15g of white crystals, yield: 90.4%, melting point: 107 -108°C.

Embodiment 2

[0022] Embodiment 2 prepares bromide salt intermediate by double imidazoline ring expansion reaction

[0023] In a four-necked flask equipped with a reflux condenser, a thermometer, and a stirrer, add 11g (0.08mol) of potassium carbonate and 100ml of ethanol, heat and stir, and slowly add 6.6g (0.04mol) of bis-imidazoline dropwise at 80°C , a mixture of 7.6g (0.04mol) of 1,2-dibromoethane and 200ml of ethanol, reacted for 2 hours, cooled to 50°C, filtered off potassium carbonate, and distilled off ethanol under reduced pressure to obtain 8.4g of amber semi-solid , which is the bromide salt intermediate, add 300ml of water to dissolve in the next step, and the yield is 78.7%.

Embodiment 31

[0024] The preparation of embodiment 31,4,7,10-tetraazadodecane

[0025] In a four-neck flask equipped with a reflux condenser, a thermometer, a stirrer and a constant pressure dropping funnel, add 76g of water, stir and heat, and reflux. Add dropwise the aqueous solution 310 grams (wherein containing about 8.4g of bromine salt intermediate, 0.03mol) and 30%NaOH aqueous solution 32g (containing sodium hydroxide 2.4mol) of the bromine salt intermediate prepared according to the method of embodiment 2, dropwise, Reflux for 2 hours, filter while hot, add the filtrate to a distillation flask, distill off water under reduced pressure, cool to obtain white crystals, and filter to obtain a crude product. The crude product was dehydrated and recrystallized with toluene to obtain 4.6 g of white crystals, namely 1,4,7,10-tetraazadodecane, with a GC content of 99% and a yield of 83.9%. Melting point: 111-113°C.

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Abstract

The invention relates to a preparation method of 1,4,7,10-tetraazadodecane, which comprises the following steps: (1) reacting triethylenetetramine and N,N-dimethylformamide dimethyl acetal in a solvent benzene at 75-85 DEG C to generate diimidazoline; (2) in the presence of potassium carbonate, reacting the diimidazoline with 1,2-ethylene dibromide in a solvent ethanol to prepare the amber semisolid bromine salt intermediate; and (3) reacting the bromine salt intermediate with sodium hydroxide in a solvent water to generate the 1,4,7,10-tetraazadodecane. The technical process is simple and convenient to operate; the total yield of the target product exceeds 60%; and thus, the invention is suitable for industrial large-scale production.

Description

technical field [0001] The invention relates to a preparation method of 1,4,7,10-tetraazadodecane. Background technique [0002] 1,4,7,10-tetraazadodecane; CAS: 294-90-6 Molecular formula: C 8 h 20 N 4 , Molecular weight: 172.28, white crystal. 1,4,7,10-Tetraazadodecane is a precursor for the synthesis of macrocyclic chelators for metal ions. [0003] At present, the synthetic methods of 1,4,7,10-tetraazadodecane mainly include Stetter method, Richman-Atkins method, Weisman method and glyoxal condensation method, among which the acetal method is used to prepare 1, 4,7,10-Tetraazadodecane has easy-to-obtain raw materials, mild conditions, and convenient operation. It is an ideal method for laboratories and production. [0004] Chinese invention patent publication CN1343203A discloses a method for preparing the compound of formula (I), 1,4,7,10-tetraazadodecane, which adopts the following route: [0005] [0006] Wherein: in step a), the condensate of triethylenetetra...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D257/02
Inventor 吴健明
Owner 太仓市茜泾化工有限公司
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