[CH3:1][CH:2]1[CH2:6][NH:5][C:4](=S)[NH:3]1.CI.[Cl:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][NH2:16])=[CH:13][CH:12]=1.[Na].[N:20](=[C:22]([C:28]#[N:29])[C:23](OCC)=[O:24])[OH:21]>CCO>[NH2:29][C:28]1[N:16]([CH2:15][C:14]2[CH:17]=[CH:18][C:11]([Cl:10])=[CH:12][CH:13]=2)[C:4]2[N:5]([CH2:6][CH:2]([CH3:1])[N:3]=2)[C:23](=[O:24])[C:22]=1[N:20]=[O:21]To a stirred suspension of 4-methylimidazoline-2-thione (45.0 g., 0.387 mole; purified by water recrystallization) in ethanol (200 ml., dried over 4A molecular sieve), methyl iodide (54.9 g., 0.387 mole) was added dropwise. The reaction was stirred at room temperature for 4 hr. during which time the solid dissolved. To this solution 4-chlorobenzylamine (54.8 g., 0.387 mole) was added and the solution was heated at reflux for 16 hrs. This solution was added while hot to a solution of sodium (35.6 g., 1.55 gram atom) in ethanol (900 ml., dried over 4A molecular sieve), and ethyl oximinocyanoacetate (5.50 g., 0.387 mole) was added in portions. The mixture was refluxed for 3 hrs. and concentrated in vacuo. Water (600 ml.) was added to the residue and the solution neutralized with HOAc. The orange precipitate was collected, washed with CH3CN and Et2O to give 95.6 g. (77%) orange solid, m.p. 222° -223° (dec.).
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