[OH-].[Na+].[S:3]1[C:7]2[CH:8]=[C:9]([CH2:12][C:13]#[N:14])[CH:10]=[CH:11][C:6]=2[N:5]=[CH:4]1.Br[CH2:16][CH2:17]Cl>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O>[S:3]1[C:7]2[CH:8]=[C:9]([C:12]3([C:13]#[N:14])[CH2:17][CH2:16]3)[CH:10]=[CH:11][C:6]=2[N:5]=[CH:4]150% aqueous sodium hydroxide (1.51 mL) was added to a mixture of 1,3-benzothiazol-6-ylacetonitrile (586 mg, 3.36 mmol), 1-bromo-2-chloroethane (335 mg, 4.04 mmol), benzyltriethylammonium chloride (76.6 mg, 3.36 mmol) at 50° C. The reaction mixture was stirred at 50° C. for 3 h. Water was added and the mixture was extracted with ethyl acetate. The combined organic layer was washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was flash chromatographed on a silica gel column with ethyl acetate in hexane from 0-30% to afford the desired product (157 mg, 24%). Analytical LCMS: (M+H)+=201.2.
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