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.
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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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