Synthetic method of iron-catalyzed phenothiazine compound
A technology of phenothiazine and synthesis method, which is applied in the field of synthesis of phenothiazine compounds, can solve the problems of slow reaction, unsuitability for mass production, limitation and the like, and achieves the effects of short reaction time, good industrialization prospect and mild conditions
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Embodiment 1
[0019] Add N-(2-mercaptophenyl)acetamide (0.3mmol, 50.1mg), FeSO 4 ·7H 2 O (0.06mmol, 16.68mg), 1,10-linphenanthroline (0.06mmol, 10.8mg) and potassium tert-butoxide (1.2mmol, 134.4mg), protected the reaction system with nitrogen gas (exhausted three times), and used 1,2-Dibromobenzene (0.45mmol, 105.2mg) and DMF (2mL) were added to the reaction system by syringe, heated to 135°C, and stirred for 24h. After the reaction was completed, it was cooled to room temperature, 20 mL of water was added and extracted three times with ether, the organic phase was washed with water, dried with anhydrous sodium sulfate, spin-dried, and the product 10H-phenothiazine was obtained by column chromatography. Yield 70%. 1 HNMR (400MHz, DMSO-d 6 ), (ppm): 8.58 (s, 1H), 7.00-6.96 (m, 2H), 6.91-6.89 (d, J=7.6, 2H), 6.76-6.68 (m, 4H), 13 CNMR (100MHz, DMSO-d 6 ), (ppm): 142.57, 128.01, 126.70, 122.23, 116.81, 114.89, LC-MS: [M+H] + m / z = 200.0.
Embodiment 2
[0021] Adopt the method in similar embodiment 1, replace the o-dibromobenzene in embodiment 1 with o-bromoiodobenzene, o-bromochlorobenzene, o-chloroiodobenzene, o-dichlorobenzene respectively, obtain the yield of product phenothiazine respectively It's 72%, 81%, 80%, 20%.
Embodiment 3
[0023] Using a similar synthesis method, 2-bromo-4-methyliodobenzene was used instead of o-dibromobenzene in Example 1 to obtain 2-methyl-10H-phenothiazine with a yield of 19%. 1 HNMR (400MHz, DMSO-d 6 ), (ppm): 8.50(s, 1H), 6.99-6.95(m, 1H), 6.90-6.88(m, 1H), 6.79-6.67(m, 3H), 6.59-6.51(m, 2H), 2.15 (s,3H), 13 CNMR (100MHz, DMSO-d6), (ppm): 142.61, 142.48, 137.36, 127.90, 126.68, 126.49, 122.95, 122.11, 117.09, 115.57, 114.89, 113.41, 21.13. LC-MS: [M+H] + m / z = 214.1.
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