[H-].[Na+].[S:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[CH:8]=[C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][C:10]1=[O:18].Cl[CH2:20][CH2:21][N:22]=[C:23]=[S:24]>O1CCCC1>[S:24]1[CH2:20][CH2:21][N:22]=[C:23]1[N:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9](=[CH:8][C:4]2[S:3][CH:7]=[CH:6][CH:5]=2)[C:10]1=[O:18]To a stirred suspension of NaH (0.51 gm; 21.1 mmole) in dry tetrahydrofuran (100 ml) is added dropwise a solution of 3-(2-thienylmethylene)-indolin-2-one prepared as described above (4.0 gm; 17.6 mmole) in dry tetrahydrofuran (100 ml). The resultant solution is stirred at room temperature for another hour, after which, it is cooled to 0° C in an ice bath, and a solution of chloroethylisothiocyanate (2.2 gm; 17.6 mmole) in dry tetrahydrofuran (50 ml) is added. The mixture is then heated at reflux temperature for 3.5 hours.
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