Ammonia → 6-Amino-2-(3-methoxy-5-methylphenylthio)benzenecarbonitrile

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A solution of 0.1 g (0.00037 mol) of 2-fluoro-6-[(3-methyl-5-methoxyphenyl)thio]benzonitrile (Example 23) in 10 mL of absolute ethanol and ca. 2 mL of THF was saturated with ammonia. The resultant solution was sealed in a glass-lined Parr bomb and heated to 145° C. for 48 h. The solvent was removed in vacuo. 20 mL of 1 NaOH was added. This aqueous solution was extracted with 3×20 mL of EtOAc. The EtOAc solution was dried over MgSO4. After solvent removal, the crude product was chromatographed on silica gel (flash; CH2Cl2), resulting in 0.03 g (30%) of 2-amino-6-[(3-methyl-5-methoxyphenyl)thio]benzonitrile as a white solid: mp 108°-110° C.; NMR (Me2SO-d6, 200 MHz) δ 2.32 (s, 3H), 3.78 (s, 3H), 6.28 (br s, 1H), 6.4 (apparent d, 1H), 6.7-6.8 (m, 2H), 6.8-6.9 (narrow m, 2H), 7.28 (apparent d, H). Anal. Calc. for C15H14N2OS: C, 66.64; H, 5.22; N, 10.36; S, 11.36. Found: C, 66.46; H, 5.22; N, 10.25; S, 11.71.

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