Thionyl Chloride → 5-(3-Chloropropyl)-2-phenylthiazole-4-carbonyl chloride
Reaction equation
O[CH2:2][CH2:3][CH2:4][C:5]1[S:9][C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:7][C:6]=1[C:16]([OH:18])=O.[Li+].[Cl-:20].S(Cl)([Cl:23])=O>>[Cl:20][CH2:2][CH2:3][CH2:4][C:5]1[S:9][C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:7][C:6]=1[C:16]([Cl:23])=[O:18]Participants
4
Procedure
A mixture of 5-(3-hydroxypropyl)-2-phenylthiazole-4-carboxylic acid (850 mg, 3.2 mmol) and LiCl (3.2 mmol) in thionyl chloride (10 mL) was heated at reflux for 16 h then concentrated to dryness. The crude product was dissolved in EtOAc, washed with brine, dried (MgSO4), and concentrated under reduced pressure to give 5-(3-chloropropyl)-2-phenylthiazole-4-carbonyl chloride (906 mg, 99% yield).