Method for synthesizing 1H,1'H-(2,2'-bis-benzimidazole)-5,5'-diamine

A technology of bisbenzimidazole and dinitroaniline, which is applied in the field of synthesizing 1H,1'H-(2,2'-bisbenzimidazole)-5,5'-diamine, can solve serious pollution, unpleasant It is suitable for problems such as industrial production, and achieves the effects of high reaction yield, cheap raw materials and short synthesis route.

Active Publication Date: 2017-08-08
CHANGZHOU SUNLIGHT PHARMA
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  • Abstract
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  • Claims
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Problems solved by technology

[0004] "Molecular docking studies and synthesis of novel bisbenzimidazole derivatives as inhibitors of α-glucosidase", Musa Özil et al., "Bioorganic & Medicinal Chemistry", No. 24, pp. 5103-5114, 2016, disclosed a method using 4-nitro-o-glucosidase A method for synthesizing 1H,1'H-5,5'-dinitro-(2,2'-bisbenzimidazole) with phenylenediamine and oxalic acid under the condition of polyphosphoric acid, which will produce A large amount of acidic wastewater is seriously polluted and not suitable for industrial production

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1）

[0022] The method for synthesizing 1H,1'H-(2,2'-bibenzimidazole)-5,5'-diamine in this example has the following steps:

[0023] a. Add 600g of tetrahydrofuran, 33g of triethylamine and 55g of 2,4-dinitroaniline into the reaction flask, cool down to 5±1°C, add 19g of oxalyl chloride dropwise, and drop it in 2-3 hours. Afterwards, the temperature was raised to 15±1°C, and the reaction was complete.

[0024] Cool down to 0-5°C, add 10g of water to the reaction system, concentrate under reduced pressure to recover tetrahydrofuran, add 250g of water and 50g of methanol, adjust the temperature to 50-60°C, stir for 2h, cool and crystallize, filter, and dry to obtain 59.9g of N, N'-bis(2,4-dinitrophenyl)oxalamide, the yield is 95.3%, the purity is 99.1% (HPLC), and the melting point is 171-174°C.

[0025] b. Add 42g of N,N'-bis(2,4-dinitrophenyl) oxalamide, 100mL of DMF, 100mL of methanol and 3g of active nickel catalyst into the autoclave, replace with nitrogen three times, and then...

Embodiment 2）

[0030] The method for synthesizing 1H,1'H-(2,2'-bibenzimidazole)-5,5'-diamine in this example has the following steps:

[0031] a. Add 580mL of dichloromethane, 36.5g of diisopropylethylamine and 50g of 2,4-dinitroaniline to the reaction flask, cool down to 5±1°C, add dropwise 17.1g of oxalyl chloride, 2 After ~3 hours of dripping, the temperature was raised to 15±1°C after the dripping, and the reaction was complete.

[0032] Cool down to 0-5°C, add 180g of water to the reaction system, adjust the temperature to 20-30°C, stir for 1h, concentrate under reduced pressure to recover dichloromethane, cool and crystallize, filter, and dry to obtain 53.9g of N,N'-bis( 2,4-dinitrophenyl) oxamide, the yield is 95.3%, the purity is 99.2% (HPLC), and the melting point is 172-175°C.

[0033] b. Add 37.8g of N,N'-bis(2,4-dinitrophenyl)oxalamide, 100mL of DMF and 0.8g of 5wt% palladium-carbon catalyst into the autoclave, replace it with nitrogen three times, and then Charge hydrogen to a...

Embodiment 3）

[0038] The method for synthesizing 1H,1'H-(2,2'-bibenzimidazole)-5,5'-diamine in this example has the following steps:

[0039] a. Add 600g of toluene, 25g of pyridine and 55g of 2,4-dinitroaniline to the reaction flask, cool down to 5±1°C, add 19.1g of oxalyl chloride dropwise, and finish dropping in 2-3 hours. Raise the temperature to 15±1°C, and the reaction is complete.

[0040] Cool down to 0-5°C, add 250g of water to the reaction system, adjust the temperature to 50-60°C, stir for 2h, cool to crystallize, filter, and dry to obtain 58.6g of N,N'-bis(2,4-dinitrobenzene base) oxamide, the yield is 92.8%, the purity is 99.3% (HPLC), and the melting point is 172.5~175°C.

[0041] b. Add 42g of N,N'-bis(2,4-dinitrophenyl)oxalamide, 100mL of DMAc, 100mL of ethanol and 1.3g of 3wt% palladium carbon catalyst into the autoclave, and replace it with nitrogen first Three times, then filled with hydrogen to a pressure of 0.6-0.8MPa, controlled the temperature at 50-60°C, kept the t...

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PUM

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Abstract

The invention discloses a method for synthesizing 1H, 1'H-(2,2'-bis-benzimidazole)-5,5'-diamine. The method comprises the steps of obtaining N,N'-bis(2,4-dinitrophenyl)oxamide through condensation reaction between oxalyl chloride and 2,4-dinitraniline, obtaining N,N'-bis(2,4-diaminophenyl)oxamide through catalytic hydrogenation of the N,N'-bis(2,4-dinitrophenyl)oxamide and obtaining the 1H,1'H-(2,2'-bis-benzimidazole)-5,5'-diamine through dehydration cyclization of the N,N'-bis(2,4-diaminophenyl)oxamide. The method disclosed by the invention has a shorter synthesizing path, high technological safety, convenience to operate, lower production cost, higher reaction yield and especially smaller environmental pollution, so that the method is suitable for industrial production; in addition, raw materials of the method are cheap and easy to obtain.

Description

technical field [0001] The invention belongs to the technical field of bisbenzimidazole, and in particular relates to a method for synthesizing 1H,1'H-(2,2'-bisbenzimidazole)-5,5'-diamine. Background technique [0002] Benzimidazole is a benziheterocyclic compound containing two nitrogen atoms. Benzimidazole derivatives and their metal complexes have good biological activity and special chemical properties, and can be used for both drug synthesis and polymerization The preparation of things. Benzimidazole polymers have excellent mechanical properties, chemical resistance, high temperature resistance, and flame resistance, and are widely used in aerospace and high-performance electronic materials. [0003] 1H,1'H-(2,2'-bisbenzimidazole)-5,5'-diamine is a new type of benzimidazole diamine monomer used in polymer synthesis, which can be used to synthesize new polyamide Imine, polyamide, polyether, silicone based polymers. [0004] "Molecular docking studies and synthesis of ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D235/20
CPCC07D235/20
Inventor 胡国宜胡锦平吴建华张培峰奚小金
Owner CHANGZHOU SUNLIGHT PHARMA
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