[H-].[Na+].[OH:3][C:4]1[CH:17]=[C:16]2[C:7]([NH:8][C:9]3[C:14]([S:15]2)=[CH:13][CH:12]=[CH:11][CH:10]=3)=[C:6]2[CH:18]=[CH:19][CH:20]=[CH:21][C:5]=12.[CH3:22][O:23][CH2:24]Cl.C(OCC)C>C1COCC1.O>[CH3:22][O:23][CH2:24][O:3][C:4]1[CH:17]=[C:16]2[C:7]([NH:8][C:9]3[C:14]([S:15]2)=[CH:13][CH:12]=[CH:11][CH:10]=3)=[C:6]2[CH:18]=[CH:19][CH:20]=[CH:21][C:5]=12
Sodium hydride (75 mg) was added to a solution of 5-hydroxy-12H-benzo[a]phenothiazine (1) (500 mg) and chloromethyl methyl ether (154 mg) in THF (10 ml) and the reaction mixture was stirred for 15 minutes. Diethyl ether (60 ml) was added to the reaction mixture followed by water (60 ml). The ether layer was decanted, dried and evaporated to dryness. The resulting residue was chromatographed on silica gel (CH2Cl2 /hexane (7:3)) to afford the title compound, m.p. 103° C. Anal. C18H15NO2S; Calcd.: C, 69.87; H, 4.89; N, 4.53; S, 10.36. Found: C, 69.75; H, 5.01; N, 4.41; S, 10.53.
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