Diaminodicarboxylic acid and its intermediate
A technology of amino and divalent hydrocarbon groups, which is applied in the field of diaminodicarboxylic acids and their salts, and can solve problems such as synthesis examples that have not been reported.
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[0048] [Preparation method of dicarbamoyl dicarboxylic acid and salt thereof]
[0049] Below with respect to dicarbamoyl dicarboxylic acid (in general formula (1), R 1 and R 2 Any one of them is a carboxyl group and the other is a carbamoyl group, R 3 and R 4 Any one of which is a carboxyl group and the other is a carbamoyl group) and the preparation method of its salt will be described.
[0050] The dicarbamoyldicarboxylic acid of this invention can be produced by making the acid dianhydride represented by General formula (5) and ammonia react.
[0051] Examples of ammonia include ammonia water, ammonia gas, and liquid ammonia.
[0052] In the case of using ammonia water, in addition to commercially available ammonia water with an ammonia content of 10 mass%, 25-28 mass% and 28-30 mass%, it can also be prepared within the range of saturation concentration at 10 mass% to reaction temperature. Ammonia water of suitable concentration.
[0053] When ammonia gas is used, it is...
Embodiment 1
[0116] (Embodiment 1) diaminobicyclo [2.2.2] octa-7-ene dicarboxylic acid dihydrochloride (in general formula (8), R 1 and R 2 Any one of them is carboxyl, the other is amino, R 3 and R 4 Any one of them is carboxyl, the other is amino, R 5 and R 6 is the preparation of the dihydrochloride of the compound of hydrogen atom)
[0117] (1) Synthesis of bicyclo[2.2.2]-oct-7-ene-2,3,5,6-tetracarboxylic diimide
[0118] At 90°C, to 124.10g of bicyclo[2.2.2]-oct-7-ene-2,3,5,6-tetracarboxylic dianhydride in N,N-dimethylformamide (500g) In the turbid solution, ammonia gas was introduced for 45 minutes. Stir at the same temperature for 30 minutes, add 300 g of ethyl acetate after cooling, and collect the precipitate by filtration. It was stirred in 300 g of 1 mol / L hydrochloric acid for 30 minutes, the filter residue was washed with methanol, and dried under reduced pressure to obtain 98.53 g of the target product as white crystals.
[0119] 1 H NMR (DMSO-d 6 ) δ2.96-3.08 (4H, ...
Embodiment 2
[0124] (Example 2) dicarbamoyl dicyclohexyl dicarboxylic acid (in general formula (9), R 1 and R 2 Any one of them is a carboxyl group, the other is a carbamoyl group, R 3 and R 4 Any one of them is a carboxyl group, the other is a carbamoyl group, and B is a single bond compound)
[0125] Under water cooling, to 3.1g of dicyclohexyl-3,3',4,4'-tetracarboxylic dianhydride in the suspension of N,N-dimethylformamide (20g), feed ammonia Air for 30 minutes. It was stirred at the same temperature for 30 minutes, and further stirred at room temperature for 2 hours. After cooling with water, the precipitate was collected by filtration. 12 g of 1 mol / L hydrochloric acid was added thereto, followed by stirring for 30 minutes. The obtained solid was filtered, washed with water and methanol, and dried under reduced pressure to obtain 2.03 g of the target product as white crystals.
[0126] 1 H NMR (DMSO-d 6 )δ0.88-1.22 (4H, m), 1.35-1.65 (6H, m), 1.70-1.93 (2H, m), 1.95-2.12 (2H,...
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