ClC1C=CC(CN)=CC=1.I.CSC1NCCN=1.[O-]CC.[Na+].[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][NH:30][C:31]2[NH:32][CH2:33][CH2:34][N:35]=2)=[CH:25][CH:24]=1.[N:36](=[C:38]([C:44]#[N:45])[C:39](OCC)=[O:40])[OH:37]>CCO>[NH2:45][C:44]1[N:30]([CH2:29][C:26]2[CH:25]=[CH:24][C:23]([Cl:22])=[CH:28][CH:27]=2)[C:31]2[N:35]([CH2:34][CH2:33][N:32]=2)[C:39](=[O:40])[C:38]=1[N:36]=[O:37]To a solution of 62.30 g. 0.44 mol) of 4-chlorobenzylamine in 500 ml absolute EtOH (dried over 4A molecular sieve aluminosilicate desiccant) is added 107.40 g (0.44 mol) 2-(methylthio)-2-imidazoline hydroiodide. The mixture is heated to boiling on a steam bath in an open flask and about 150 ml of the ethanol is allowed to slowly boil off over 2 hr. This solution is added while still hot to 1.76 mole of sodium ethoxide in 1650 ml absolute EtOH. To the resulting stirred, basic solution of 2-[(4-chlorophenyl)methyl]amino-2-imidazoline is then added 61.85 g (0.44 mol) crystalline (mp 129°-131°) ethyl oximinocyanoacetate in portions. The bright yellow solution is refluxed for 3 hr and then cooled to room temperature. The yellow precipitate is collected, washed with i-PrOH, and partially air-dried. The damp sodium salt is dissolved in 2000 ml H2O and acidified with glacial HOAc. The bright pink precipitate is filtered and aid-dried overnight, then oven-dried in vacuo at 100° to yield 103.05 g (77%) of pink powder, mp 238°-241°d. Recrystallization of this material from DMF-EtOH gives red crystals, mp 241°d.
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