C([Li])CCC.[S:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[CH:7]1.C(OCC)C.[Cl:20][C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[CH:23]=[O:24]>CCCCCC>[Cl:20][C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[CH:23]([C:7]1[S:6][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=1)[OH:24]47 mL of 1.6M-butyllithium in hexane was added dropwise to a solution of benzothiazole (10 g, from Aldrich) and diethyl ether (200 mL) at -78° C. under nitrogen. The red brown solution was stirred at -78° C. for 30 min., followed by the addition of a solution of o-chlorobenzaldehyde (10.8 g) and diethyl ether (100 mL) at -78° C. The mixture was then stirred at -78° C. for 2 hours before it was allowed to warm to room temperature and stirred at room temperature overnight.
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