Oxalic Acid → 2-(1-Trityl-1h-imidazol-4-yl)-benzylamine oxalate salt

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Reaction Steps

The crude 2-(1-trityl-1H-imidazol-4-yl)-benzylamine (66.1 g, 159 mmol) was dissolved in tetrahydrofuran (420 ml). Solid oxalic acid (14.3 g, 159 mmol) was added to the solution while stirring. This mixture was stirred at room temperature for 15 min and then added dropwise to stirring hexane (2000 ml). Tetrahydrofuran (100 ml) was used to rinse the glassware. A yellow solid precipitated. The mixture was stirred for an additional 20 min and the product was isolated by filtration. The solid was rinsed with 4:1 hexane:tetrahydrofuran (625 ml) and dried in a vacuum oven at ˜45° C. with an air purge for 18 h to afford 2-(1-trityl-1H-imidazol-4-yl)-benzylamine oxalate salt; MS (ES+) M+1 416.6 for C29H25N3.

Provenance & Evidence