SYNTHESIS 



NH CN NH CN 



ii I II I 



CH3.C + C.COOCaHg > CH3.C C.COOCjH, 



I 11 I II 



NHj CHOCjHg NH— CH 



N— C . NH, 



II II 

 > CH, . C C . COOCjH^ 



I I 

 N=CH 



Another variant is provided by the following series of reactions : 



HOCH, . CHa . CN > CHgOCH, . CH, . CN 



CN CN 



llS22S^ C,H,0 . CH» i '^-'''\ C.H,0 . CH, i 



CHONa CHOOC.CH3 



N=C . NH, N=C . NH2 



cH3.C(NH,):NH^^^ I. (i.cH,OC,H,— >CH,.i i . CH.Br 



II II II II 



N— CH N— CH 



References to Section 4 



1. H. Horlein, Z. physiol. Chem., 1938, 253, 82. 



2. E. Andersag and K. Westphal, Ber., 1937, 70, 2035. 



3. R. R. Williams and J. K. Cline, /. Amer. Chem. Soc, 1936, 68, 



1504. 



4. E. R. Buchman, ihid., 1936, 58, 1803. 



5. J. K. Cline, R. R. Williams and J. Finkelstein, ihid., 1937, 59, 



1052. 



6. Research Corporation, B.P. 472396, 490571 '> U.S.P. 2216574, 



2223885, 2218349, 2218350. 



7. Research Corporation, B.P. 472459. 



8. Research Corporation, B.P. 496738, 522531. 



9. Research Corporation, B.P. 496726, 507918 ; U.S.P. 2166233. 



ga. A. J. Eusebi, E. V. Brown and L. R. Cerecedo, /. Amer. Chem. Soc, 



1949, 71. 2931. 



10. A. R. Todd, F. Bergel and KarimuUah, /. Chem. Soc, 1936, 1557. 



11. A. R. Todd and F. Bergel, ihid., 1937, 364. 



12. Hofimann-La Roche, B.P. 478993. 



13. Hofimann-La Roche, B.P. 486414. 



14. Hofimann-La Roche, B.P. 542403. 



15. Hoffmann-La Roche, B.P. 500519. 



16. Hoffmann-La Roche, B.P. 496801. 

 1 6a. Chinoin, B.P. 615404. 



21 



