Yield:38221-55-5 97%

Reaction Conditions:

in toluene at 0 - 80; for 12 h;

Steps:

2-Chloro-1-(2-(trifluoromethyl)-10H-phenothiazin-10-yl)ethanone (2)

To a solution of 2-trifluoromethyl phenathiazine 1 (2.0g, 7.49mmol) in toluene (30mL) was added chloroacetyl chloride (0.88mL, 11.23mmol) at 0°C and then heated at 80°C for 12h. The reaction mixture was cooled to rt, concentrated under reduced pressure and the crude residue was dissolved in dichloromethane (50mL), washed with water (2×50mL) dried over anhydrous sodium sulfate and evaporated to give 2-chloro-1-(2-(trifluoromethyl)-10H-phenothiazin-10-yl)ethanone (2) as white solid (2.5g, 97%). ¹H NMR (500MHz, CDCl₃) δ 7.91 (s, 1H), 7.47-7.57(m, 4H), 7.28-7.42 (m, 1H), 7.17 (d, J=7.55Hz 1H), 4.25 (d, J=12.8Hz 1H), 4.12 (d, J=12.8Hz, 1H). ¹³C NMR (75MHz, CDCl₃) δ 165.4, 138.0, 137.1, 128.9, 128.3, 128.2, 127.9, 126.1, 125.2, 123.99, 123.96, 41.5. IR (KBr) 3003, 2950, 1692, 1608, 1467, 1329, 1244, 1168, 1132, 1086, 824, 747, 641cm^-1. MS (ESI) m/z 344 [M+H]⁺.

References:

Addla, Dinesh;Jallapally, Anvesh;Gurram, Divya;Yogeeswari, Perumal;Sriram, Dharmarajan;Kantevari, Srinivas [Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,# 1,p. 233 - 236]