Hydrochloric Acid → 2,6-Dimethyl-4-[2-(2-methylphenyl)acetamido]phenyl thiocyanate

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Reaction Steps

2-(2-Methylphenyl)acetyl chloride (9.9 g, 58.8 mM) was added to a stirred suspension of calcium carbonate (7.87 g, 78.7 mM) and 4-amino-2,6-dimethylphenyl thiocyanate (7 g, 39.3 mM) in dry THF (150 mL). The mixture was stirred for 1 hour. Water (1000 mL) was added. The mixture was acidified to pH4 with 2M HCl and extracted with ethyl acetate. The combined extracts were washed with water, then with saturated sodium chloride solution and dried (MgSO4). The solvent was removed by evaporation. The pale green solid obtained was triturated with ether to give 2,6-dimethyl-4-[2-(2-methylphenyl)acetamido]phenyl thiocyanate (B), as a cream coloured solid in 83% yield; NMR (CDCl3, 200 MHz): 2.47(s, 3H), 2.49(s, 6H), 3.69(s, 2H), 7.14-7.17(m, 4H), 7.55(s, 2H), 10.27(s, 1H).

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