[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=[O:12])[C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[O:7][C:6]=2[N:17]=1.C1CCC(=C(F)CNCC2C=CC(F)=CC=2)CC1.[H-].[Na+].Cl[CH2:39][CH2:40][S:41][CH3:42]>O.CN(C)C(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH2:39][CH2:40][S:41][CH3:42])[C:10](=[O:12])[C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[O:7][C:6]=2[N:17]=1
To as suspension of 17.0g (0.069 mole) 2-Chloropyrido[2,3-b][1,4]benzoxazepin-6(5H)-one and 150 mL of N,N-dimethylacetamide was added 9.8g of sodium hydride (50%). The mixture was warmed to 60° C. for 30 minutes. To the reaction mixture 12.2g (0.11 mole) of 2-chloroethylmethylsulfide was added dropwise. The mixture was heated to 120° C. for 4 hours, then cooled to room temperature and poured into water. The crude product was purified by column chromatography using silica gel and then recrystallized from petroleum ether/benzene to yield 17.3g (78% yield) of 2-chloro-5-(methylthioethyl)pyrido[2,3-b][1,4]benzoxazepin-6(5H)-one, m.p. 126°-128° C.
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