Penicillin G Hydrabamine

Ethylenediamine (15 g, 025 mol) was added dropwise to 100 ml 98-100% formic acid in a two-necked 500 ml flask, fitted with an addition tube and reflux condenser with drying tube, cooled in an ice-bath. After complete addition of the base, 53 g of benzaldehyde (0.5 mol) was added in one lot. The ice-bath was removed and the flask was heated to the refluxing temperature. The initial rate of carbon dioxide evolution was too rapid to measure. After twenty minutes, the rate was circa 100 ml per minute and decreased rapidly to 8 ml per minute in one hour. Heating at reflux was continued for 35 hours. 

To a solution of 60 g of sodium penicillin G in 800 cc of distilled water cooled to 0°C to 4% in an ice-bath, a solution of 35 g of N,N -dibenzylethylenediamine diacetate in 200 cc of distilled water is added dropwise with stirring. The thick slurry is filtered with suction, washed twice with 100 cc of cold water, dried by suction and spread out in a thin layer for completion of drying. The product weighed 80 g. 

The air-dried powder has a broad melting point, sintering at 100°C, melting above 110°C to a cloudy liquid becoming clear at 135°C, 

Chemical Name N,N -Bis(dehydroabietyl)ethylenediamine dipenicillin G Common Name — 

A mixture of 142.5 g of Rosin Amine D containing about 70% dehydroabietylamine and 30% dihydro and tetrahydroabietylamine, 47.0 g of ethylene dibromide, and 60.6 g of tri-ethylamine is dissolved in 350 cc of anhydrous xylene and refluxed for about 16 hours. Thereafter the triethylamlne dibromide salt formed is separated from the solution by filtering the cool reaction mixture and washing with ether. The solution is then concentrated under reduced pressure to dryness to remove the ether, xylene and excess triethylamines present. 

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