Methanol → HCID 67081740, compound

Participants

Reaction Conditions

Reaction Steps

2-Amino-5-methoxythiophenol was prepared as set forth in C. A. Mathis, Y. Wang, D. P. Holt, G-F. Huang, M. L. Debnath and W. E. Klunk, “Synthesis and Evaluation of 11C-Labeled 6-Substituted 2-Arylbenzothiazoles as Amyloid Imaging Agents.” J. Med. Chem., 46, pp 2740-2754 (2003). 4-Iodobenzyl chloride (5.0 g, 18.8 mmol) was added to a hot solution of 2-amino-5-methoxythiophenol (2.32 g, 15.0 mmol) in toluene (75 mL) and the reaction mixture was stirred at 100° C. for 1 h. Methanol (1 mL) was then added to destroy the excess 4-iodobenzoyl chloride. The hot toluene solution was then passed through a pad of silica gel (˜15 g) in a Buchner funnel. The silica gel was rinsed a few more times with hot toluene. The filtrate upon concentration gave pure 2-(4-iodophenyl)-6-methoxy-1,3-benzothiazole (4) (1.65 g, 40%) as off-white crystals.

Provenance & Evidence