S(Cl)([Cl:3])=O.[N+:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[S:15][C:16]2[C:21]([N:22]=1)=[CH:20][C:19]([CH2:23]O)=[CH:18][N:17]=2)([O-:7])=[O:6].CN(C=O)C>C(Cl)Cl>[Cl:3][CH2:23][C:19]1[CH:20]=[C:21]2[N:22]=[C:14]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=3[N+:5]([O-:7])=[O:6])[S:15][C:16]2=[N:17][CH:18]=1Thionyl chloride (3.1 mol, 227 mL) was slowly added to a room temperature suspension of (2-(2-nitrophenyl)thiazolo[5,4-b]pyridin-6-yl)methanol (0.62 mol, 180 g) in CH2Cl2 (1.8 L). DMF (5 mL) was added and the reaction became homogeneous. The reaction was stirred for 1 h, then concentrated under reduced pressure. The crude product was dissolved in CH2Cl2 (150 mL) and concentrated under reduced pressure. The crude product was chased with hexane (200 mL×3)) and dried under vacuum for 16 h to give 6-(chloromethyl)-2-(2-nitrophenyl)thiazolo[5,4-b]pyridine as a tan solid (180 g, 94% yield).
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