Preparation method of phenyltriazine compound and preparation method of phenylpyridine compound
A technology of phenyltriazine and compound, which is applied in the field of compound synthesis, can solve the problems of low yield, and achieve the effects of low cost, easy industrial production, and good process controllability
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[0049] The invention provides a kind of preparation method of phenyl triazine compound, comprises the following steps:
[0050] Mix the compound having the structure represented by formula (I), the compound having the structure represented by formula (II), organic protic acid, ammonium salt and the first organic solvent, and react at 50-200°C for 2-48 hours to obtain The phenyl triazine compound of structure shown in formula (Ⅲ);
[0051]
[0052] Wherein, X is selected from one of halogens;
[0053] R 1 and R 2 independently selected from phenyl or phenyl containing substituents selected from alkyl, alkoxy, fluorine, chlorine, bromine, hydroxyl, nitro, cyano, amino, amido, carboxyl, ester and one or more of the acyl groups.
[0054] In the present invention, X is preferably chlorine or bromine;
[0055] The R 1 It is preferably phenyl or phenyl containing a substituent, and the substituent is selected from an alkyl group with 1 to 5 carbon atoms, an alkoxy group with...
Embodiment 1
[0105] Add α-bromoacetophenone (19.9g, 0.1mol), phenylhydrazine (13.6g, 0.1mol), acetic acid (36g, 0.6mol), ammonium acetate (46.2g, 0.6mol) and dimethyl Sulfoxide (500ml), the reaction mixture was heated to 150°C, reacted for 15h, the product was precipitated, filtered, and dried to obtain 3,6-diphenyl-1,2,4-triazine (22.2g, yield 95%, Purity (HPLC)>99.0%), directly used in the next step reaction.
[0106] Add 3,6-diphenyl-1,2,4-triazine (22.2g, 0.095mol), norbornadiene (27.6g, 0.3mol) and trimethylbenzene (200ml) obtained in the previous step reaction into the reactor , heated to 160°C, and reacted for 15h. After the reaction was completed, it was cooled to room temperature and filtered to obtain 21.3 g of 2,5-diphenylpyridine (97% yield, purity (HPLC)>99.0%). 1HNMR (300MHz, DMSO) δ8.94(s, 1H), 8.05(d, 2H), 7.95(d, 1H), 7.81(d, 1H), 7.64(d, 2H), 7.50(t, 4H), 7.42 (dd, 2H).
Embodiment 2
[0108] Add α-chloro-4-methoxyacetophenone (18.4g, 0.1mol), 4-methoxyphenylhydrazide (16.6g, 0.1mol), propionic acid (29.6g, 0.4mol), Ammonium propionate (36.4g, 0.4mol) and methylpyrrolidone (500ml), the reaction mixture was heated to 190°C, reacted for 36h, the product precipitated out, filtered and dried to obtain 3,6-bis(4-methoxyphenyl )-1,2,4-triazine (27.5 g, yield 94%, purity (HPLC)>99.0%) was directly used in the next reaction.
[0109]Add 3,6-bis(4-methoxyphenyl)-1,2,4-triazine (27.5g, 0.094mol) and norbornadiene (46.1g, 0.5mol) obtained in the reaction in the previous step into the reactor ) and xylene (200ml), heated to 130°C and reacted for 18h. After the reaction was completed, it was cooled to room temperature and filtered to obtain 25.2 g of 2,5-bis(4-methoxyphenyl)pyridine (92% yield, purity (HPLC)>99.0%). 1H NMR (300MHz, CDCl3) δ8.88(d, 1H), 8.0(d, 2H), 7.92(d, 1H), 7.73(d, 1H), 7.52(d, 2H), 7.29(d, 2H) , 7.01 (d, 2H), 3.87 (s, 6H).
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