1910-85-6

1-Chlorophenothiazine is used in electronic structure and physical-chemical properties relationship for phenothiazine derivatives by quantum chemical calculations.

The general procedure for the synthesis of 1-chloro-10H-phenothiazine from 1,2-dichloro-3-iodobenzene and S-(2-acetamidophenyl) thioacetate was as follows: to an oven-dried 25 mL milled-mouth test tube fitted with a stirrer was added sequentially S-(2-acetamidophenyl) thioacetate (0.5 mmol), 1,2-dichloro-3-iodobenzene (0.6 mmol) , Cs2CO3 (2.0 mmol) and DMF (3 mL). The test tube was sealed with a sleeve rubber stopper, evacuated and replaced with argon for three cycles. The reaction mixture was stirred at 130°C for 10 hours. After completion of the reaction, it was cooled to room temperature, the reaction was quenched with water (20 mL) and extracted three times with ethyl acetate (20 mL). The organic layers were combined, dried with anhydrous MgSO4 and subsequently concentrated under vacuum on a rotary evaporator. Finally, the residue was purified by silica gel column chromatography using gradient elution (eluent: petroleum ether/ethyl acetate) to afford the target product 1-chloro-10H-phenothiazine.

[1] Synthetic Communications, 2017, vol. 47, # 7, p. 710 - 715