Benzenamine, 4-methyl-, hydrochloride (1:1) → 1,2-Ethanediamine, N-(4-methylphenyl)-
Reaction equation
Cl.[CH3:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.O1[CH2:14][CH2:13][NH:12]C1=O>COCCOCCO>[CH3:2][C:3]1[CH:9]=[CH:8][C:6]([NH:7][CH2:14][CH2:13][NH2:12])=[CH:5][CH:4]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 170 °C
Procedure
A mixture of 4-methylaniline hydrochloride (15.0 g, 0.10 mole), 2-oxazolidinone (8.7 g, 0.10 mole) and 40 ml of 2-(2-methoxyethoxy)ethanol was heated in an oil bath to 170° C. for four hours. On cooling to room temperature, a solid formed. Workup as described in Examples 1 and 8, followed by distillation at 110° C. to 120° C. (1.5 mm Hg) gave a 76 percent yield of the material as a clear liquid which slowly solidified on standing at ambient temperatures to a low-melting solid.