Carbon Dioxide → N1-(3-chlorophenyl)ethane-1,2-diamine

HRID 1702498

Reaction equation

Cl.[Cl:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6].Cl.ClC1[CH:13]=[C:14](C=CC=1)[NH2:15].O1CCNC1=O.C(=O)=O>CCOCC.O>[Cl:2][C:3]1[CH:4]=[C:5]([NH:6][CH2:13][CH2:14][NH2:15])[CH:7]=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 160 °C

Procedure

Gaseous hydrogen chloride was reacted with m-chloroaniline in ether at 0° C. to prepare the m-chloroaniline hydrochloride. This reactant (65.6 g, 0.4 mole) was then intimately mixed with 2-oxazolidinone by grinding with a mortar and pestle. The ground mixture was then added to a 250 ml flask equipped with a mechanical stirrer and gas vent. The flask was heated in an oil bath to 160° C. with stirring. The solid mixture melted and CO2 evolution commenced in about 15 minutes. Heating was continued for about six hours whereupon the flask was cooled and the contents dissolved in water and filtered. The filtrate was then basified with aqueous caustic causing a yellow oil to separate. Extraction with methylene chloride, drying and distillation under vacuum gave 55 g (80 percent yield) of N-(3-chlorophenyl)-1,2-ethanediamine.

Workup

customby grinding with a mortar and pestle
additionThe ground mixture was then added to a 250 ml flask
customequipped with a mechanical stirrer
temperatureHeating
temperaturewas cooled
filtrationfiltered
customto separate
extractionExtraction with methylene chloride
customdrying
distillationdistillation under vacuum

Sources & evidence

ORD record: ord-4bf60c0eb8284bb6b3abd21ffe2f09cc
Source dataset: uspto-grants-1983_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04381401

Linked notes

Loading…