Carbon Dioxide → N~1~-(4-Methoxyphenyl)ethane-1,2-diamine
Reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1.O1[CH2:15][CH2:14][NH:13]C1=O.C(=O)=O>COCCOCCO>[CH3:2][O:3][C:4]1[CH:10]=[CH:9][C:7]([NH:8][CH2:15][CH2:14][NH2:13])=[CH:6][CH:5]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 175 °C
Procedure
A mixture of 4-methoxyaniline hydrochloride (17.1 g, 0.107 mole), 2-oxazolidinone (8.7 g, 0.10 mole) and 50 ml of 2-(2-methoxyethoxy)ethanol was heated to 175° C. After five hours, carbon dioxide gas evolution had ceased and the dark mixture was allowed to cool to room temperature. Neutralization in a manner similar to that described in Example 1, and distillation at 130° C. to 140° C. (0.5 mm Hg) afforded a 45 percent yield of the amine as a colorless liquid which slowly solidified on standing at ambient temperature to a low-melting solid.
Workup
- temperatureto cool to room temperature
- distillationNeutralization in a manner similar to that described in Example 1, and distillation at 130° C. to 140° C. (0.5 mm Hg)
Sources & evidence
- ORD record
- ord-1c37deb58198462a9f94facc94041c26
- Source dataset
- uspto-grants-1983_04
- Patent number
- US04381401
Reaction notes
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