1H-1,2,4-Triazole → 1-(3-Methyl-4-nitrophenyl)-1,2,4-triazole

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Reaction Steps

A mixture of 3-fluoro-6-nitrotoluene (50.0 g), 1,2,4-triazole (22.2 g) and sodium carbonate (34.0 g) was heated with stirring in dimethylformamide (300 cm3) at 130° for 16 hours. The cooled mixture was then concentrated in vacuo, the residue was acidified to pH1 with 4M hydrochloric acid, and the resulting solution was extracted with chloroform (2×25 cm3) to remove any neutral material. The combined aqueous phases were basified to pH10 with 2.5M sodium hydroxide solution and the mixture was extracted with chloroform (3×250 cm3). The combined and dried (MgSO4) organic extracts were concentrated in vacuo to give a solid which was recrystallised from toluene to give 1-(3-methyl-4-nitrophenyl)-1,2,4-triazole, m.p. 116°-7°.

Provenance & Evidence