[C:1]1(=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[NH2:12][C:13]([NH2:15])=[S:14].[I:16]I>O>[IH:16].[N:12]1[C:1]2[C:10]3[C:5]([CH2:4][CH2:3][C:2]=2[S:14][C:13]=1[NH2:15])=[CH:6][CH:7]=[CH:8][CH:9]=3A mixture of 1-tetralone (5.00 mL; 37.6 mmol), thiourea (5.72 g; 75.2 mmol) and iodine (9.54 g; 37.6 mmol) were heated to 95° C. with stirring. After 4 hr., the mixture solidified and was allowed to cool to room temperature. The mixture was diluted with 200 mL of water and the solid material was filtered off and triturated with absolute ethanol. The solid was washed several times with absolute ethanol to provide 4.00 g of 4,5-Dihydro-naphtho[1,2-d]thiazol-2-ylamine hydroiodide 15 as an off white powder.
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