Thiourea → 4-(2-Aminothiazol-4-yl)-3,5-dimethylphenol

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Reaction Steps

A mixture of 2-bromo-1-(4-hydroxy-2,6-dimethylphenyl)ethanone (5-1, 2.43 g, 10.0 mmol) and thiourea (1.37 g, 18.0 mmol) in 95% EtOH (30 mL) was heated at reflux for 120 min. The solution was concentrated and added with water (50 mL) and saturated aqueous Na2CO3 (5.0 mL). The resultant precipitate was filtered and washed with a solution of 50% EtOAc in hexanes. The solids were dried under vacuum to give 4-(2-aminothiazol-4-yl)-3,5-dimethylphenol (5-2, 1.74 g) as pale yellow solids in 79% yield: 1H NMR (500 MHz, CDCl3) δ 8.7 (s, 2 H), 6.17 (s, 2 H), 5.97 (s, 1 H), 1.71 (s, 6 H).

Provenance & Evidence