Br.N=[C:3]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:6][CH2:5][S:4]1.C([O-])(=[O:17])C.[Na+].C(O)(=O)C.N([O-])=O.[Na+]>O>[C:9]1([CH2:8][N:7]2[CH2:6][CH2:5][S:4][C:3]2=[O:17])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1
To a solution of 2.73 g (0.01 mol) of 2-imino-3-phenylmethylthiazolidine hydrobromide in 10 ml of water 1.36 g of anhydrous sodium acetate and 0.62 ml of glacial acetic acid are added, then 0.75 g of sodium nitrite dissolved in 3 ml of water is dropped to the above mixture at 5° C. under stirring, then the mixture is stirred at 5° C. for additional 3 hours. After standing in a refrigerator overnight, the solution is stirred at room temperature for 3 hours. After rubbing, a precipitate appears which is filtered off, washed with water, dried and then refluxed with five volumes of n-butanol for 2 hours. After evaporating the solvent, the residue is thoroughly rubbed with diisopropyl ether and the product is filtered off. Thus, 0,81 g (42.3%) of the title product is obtained, m.p.: 49°-50° C.
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