3,4-Diaminotoluene → HCID 87732527, compound

Participants

Reaction Steps

A solution of 1,1′-thiocarbonyldiimidazole (26 mg, 0.13 mmol) in acetonitrile (1 mL) and pyridine (1 mL) was cooled to about −20 C and a solution of Example 395 (60 mg, 0.09 mmol) in acetonitrile (1 mL) and pyridine (1 mL) was added dropwise. The reaction mixture was stirred for about 2.5 hours while being allowed to warm to room temperature, then 3,4-diaminotoluene (25 mg, 0.2 mmol) was added and the solution was stirred at about 35 C for about 2 days. The mixture was evaporated to dryness and the residue was purified by flash column chromatography on silica gel using dichloromethane/methanol (10:1) as eluent to provide Example 605. MS (ESI): m/z 771 (M+H)+.

Provenance & Evidence