Iodoethane → HCID 13784682, compound

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH:17]2[C:22](=[O:23])[NH:21][C:20]3[CH:24]=[CH:25][CH:26]=[CH:27][C:19]=3[S:18]2)[CH2:11][CH2:10]1.[H-].[Na+].[CH2:30](I)[CH3:31]>CN(C)C=O>[CH2:30]([N:21]1[C:20]2[CH:24]=[CH:25][CH:26]=[CH:27][C:19]=2[S:18][CH:17]([CH2:16][CH2:15][N:12]2[CH2:11][CH2:10][N:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[O:2][CH3:1])[CH2:14][CH2:13]2)[C:22]1=[O:23])[CH3:31]

Participants

Procedure

In a solution of 1.0 g of 2-[2-[4-(2-methoxyphenyl)-1-piperazinyl]ethyl]-2H-1,4-benzothiazin-3(4H)-one, in 10 ml of dimethylformamide, was added 120 mg of 60% sodium hydride in oil at room temperature with stirring. The mixture was stirred for 10 minutes and 480 mg of ethyl iodide was added thereto. The whole mixture was stirred for further two hours, poured into ice-water and extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4), and concentrated. The residue was subjected to a column chromatography on silica-gel (50 g). From the eluate with hexane-ethyl acetate (2:1, v/v) was obtained 4-ethyl-2-[2-[4-(2-methoxyphenyl)-1-piperazinyl]ethyl]-2H-1,4-benzothiazin-3(4H)-one as an oily substance (0.60 g). This product was crystallized as the hydrochloride. The yield was 0.50 g (39%). Recrystallization from methanol-ether gave colorless prisms, m.p. 142°-144° C.