Benzenamine, 4-methyl-, hydrochloride (1:1) → 1,2-Ethanediamine, N-(4-methylphenyl)-

HRID 1702497Notes

Reaction equation

HRID 1702497 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]=1

Participants

4

Reactant 2

HCID 10891Benzenamine, 4-methyl-, hydrochloride (1:1)HCID 739492-Oxazolidinone

Product 1

HCID 144411411,2-Ethanediamine, N-(4-methylphenyl)-Yield 76%

Reagents, catalysts & solvents 1

HCID 8134Diethylene Glycol Monomethyl EtherSolvent

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.

Workup

  1. temperatureOn cooling to room temperature
  2. customa solid formed
  3. distillationfollowed by distillation at 110° C. to 120° C. (1.5 mm Hg)

Sources & evidence

ORD record
ord-dba9b8a3b28347a091c579c35f9d76c2
Source dataset
uspto-grants-1983_04
Patent number
US04381401

Reaction notes

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