Ethylenediamine → Ammonia

Temperature

70 °C

Sodium (4.98 g, 216.7 mmol) was added to methanol (100 ml), and was allowed to react, the mixture was evaporated. 3.5-Dichloropyridine (25.0 g, 166.7 mmol) and dimethyl sulfoxide (250 ml) were added. The mixture was stirred at 70° C. overnight. Aqueous sodium hydroxide (500 ml, 1 M) was added, and the mixture was extracted twice with diethyl ether (500 ml). The crude mixture was stirred together with ethylenediamine (50.0 g, 833.5 mmol), potassium tert-butoxide (37.4 g, 333.4 mmol) and 1,2-dimethoxyethane (500 ml) at reflux for 4 h. Aqueous sodium hydroxide (1 l, 1 M) was added, and the mixture was extracted five times with ethyl acetate (500 ml). Chromatography on silica gel with dichloromethane, methanol and conc. ammonia (89:10:1) gave the title compound as free base. Yield 13.0 g, 47%.

1. customto react
2. customthe mixture was evaporated
3. extractionthe mixture was extracted twice with diethyl ether (500 ml)
4. temperatureat reflux for 4 h
5. extractionthe mixture was extracted five times with ethyl acetate (500 ml)

ORD record

ord-f9e99c57c5514b1cb229484f8a0e12ab

Source dataset

uspto-grants-2004_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06825189B1