Sodium ethanethiolate → 5-(Ethylthio)-3-(2-methyl-3-nitrophenyl)-1,2,4-triazin-6-amine

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Reaction Steps

To a solution of 5-chloro-3-(2-methyl-3-nitrophenyl)-1,2,4-triazin-6-amine (Ex. 1, A) (1.34 g, 5.04 mmol) in DMF (30 mL) at 0° C. was added sodium ethanethiolate (0.509 g, 6.05 mmol) in one portion. The resulting mixture was stirred at rt for 1 hr before it was diluted with ethyl acetate (300 mL) and washed sequentially with 5% NaHCO3 (50 mL), water (2×50 mL), and brine (50 mL). The organic layer was dried over anhydrous MgSO4 and concentrated under vacuum. The product, 5-(ethylthio)-3-(2-methyl-3-nitrophenyl)-1,2,4-triazin-6-amine (1.333 g, 4.58 mmol, 91% yield), was isolated as a yellow solid by ISCO (120 g silica gel, solid loading, 2-5% MeOH/CH2Cl2).

Provenance & Evidence