Graduate Thesis Or Dissertation
 

The chlorination of uric acid by phosphorus oxychloride in the presence of certain aliphatic and aromatic amine hydrochlorides

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  • Since the use of N, N-diethylaniline hydrochloride in the chlorination of uric acid with phosphoryl chloride seems to promote the reaction, a study of the effect of other salts of nitrogenous bases in the chlorination of uric acid was undertaken. When N, N-diethylaniline hydrochloride was used in lieu of the free base, the yield of 2, 6, 8-trichloropurine ranged from 41-51%. To further test the use of amine salts, triethylamine hydrochloride was tested as the amine hydrochloride. Under completely anhydrous conditions, the yield of 2, 6, 9-trichloropurine ranged from a trace to 1.5%. When known amounts of water were introduced into the reaction mixture, the yield of 2, 6, 8-trichloropurine showed a marked increase. The yields of 2, 6, 8-trichlorpurine ranged from 26.2% when 10 microliters of water was added to 41.0% when 0.7 milliliters of water was introduced. In all cases where water was added to the reaction mixture no uric acid was recovered from the reaction products. Also, in no case was the water present as such but reacted immediately with the phosphoryl chloride to yield "pyrophosphoryl chloride." The results from previous experiments using N, N-diethylaniline hydrochloride strongly indicated that either the presence or absence of water had a marked effect on the yield of trichloropurine. Thus when water was introduced into the chlorination reaction with uric acid, phosphorus oxychloride, and N, N-diethylaniline hydrochloride, the yield of 2, 6, 8-trichloropurine dropped to 23.9% with no recovered uric acid. Other amine hydrochlorides were tried in the chlorination reaction with some being made in situ. N, N-dimethyl-p-toluidine hydrochloride gave only 28.3% of trichloropurine whereas N, N-dimethylaniline gave a 43.3%yield of 2, 6, 8-trichloropurine. In general it was found that anhydrous tertiary aromatic amine hydrochlorides definitely increase the yield of 2, 6, 8-trichloropurine and aliphatic tertiary amine hydrochlorides with known amounts of water added also give relatively high yields of trichloropurine. In all cases, the reaction was much cleaner and free from colored side products which appear when the free amine is used in the chlorination of uric acid.
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