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13. General procedure for the copper-catalyzed S-Arylation of 2-
Mercaptobenzothiazoles with Aryl Iodides in Water: To a 10 mL
sealed tube with a stir bar was added CuI (0.05mmol), Aryl iodides
(0.6 mmol), 2-mercaptobenzothiazoles (0.5 mmol), Na2CO3 (1.0
mmol), H2O (2 mL) and the mixture was stirred for 24 h at 100 C.
The mixture was then cooled to r.t. and extracted with EtOAc (3 × 10
mL). The organic layers were combined, washed with sat. brine (2 ×
10 mL), dried (Na2SO4), filtered, and concentrated under reduced
pressure. The crude product was purified by column chromatography.
Selected spectral data for 4-(benzo[d]thiazol-2-ylthio)aniline (Table 2,
1
entry 11): H NMR (300 MHz, CDCl3): = 6.74-6.77 (d, J = 8.0 Hz,
2H), 7.21-7.24 (t, 1H), 7.36-7.39 (t, 1H), 7.49-7.52 (d, J = 8.0 Hz,
2H, ), 7.62-7.63(d, J = 8.0 Hz, 1H), 7.83-7.85 (d, J = 8.0 Hz, 1H). 13
C
NMR (75 MHz, CDCl3): = 115.9, 116.8, 120.7, 121.6, 123.9, 126,
135.4, 137.6, 148.8, 154.3, 173.3.
5