Toluene → HCID 86653327, compound

Participants

Reaction Steps

In a round bottom flask, 1-(4-methoxy-benzyl)-1H-pyrazole-3,5-dicarboxylic acid 5-methyl ester (105, 5.48 g, 18.9 mmol) was combined with 20 mL of toluene and thionyl chloride (6 mL, 80 mmol). The reaction was heated at reflux for 40 minutes, then concentrated 2× from toluene and the resulting solid dried under vacuum. This was dissolved in 30.0 mL of acetone and sodium azide (3.8 g, 58 mmol) in 10.0 mL of water was added and stirred for 1 minute. The reaction was poured into 250 mL of ice water and stirred slowly. The resulting precipitate was collected by filtration and dried under vacuum to provide the desired compound.

Provenance & Evidence