Sodium Hydroxide → HCID 67297682, compound

Participants

Reaction Steps

2-tert-butyl-N-(chloro(p-tolyl)methylene)benzenamine (HS Imine II) (2.86 g, 10 mmol) was dissolved in 50 mL of toluene. 2-tert-butylaniline (1.56 mL, 10 mmol) was added dropwise at room temperature, resulting in a yellow solution, which was refluxed overnight. Toluene was removed under vacuum. Sodium hydroxide (100 mL of 0.10 M solution, 10 mmol) was added and the solution was stirred for 1 hour. The solid that deposited was extracted into 150 mL of diethylether. The ether layer was dried with MgSO4, filtered, and taken to dryness, leaving 3.72 g (93%) of white solid. The 1H NMR spectrum is complex and is consistent with a mixture of E/Z isomers.

Provenance & Evidence