[CH3:1][N:2]([CH3:11])[C:3](=[O:10])[C:4](=[N:8]O)[C:5](=O)[CH3:6].[H][H].[O-:14][C:15]#[N:16].[K+]>C(O)C.Cl.O>[O:14]=[C:15]1[NH:16][C:5]([CH3:6])=[C:4]([C:3]([N:2]([CH3:11])[CH3:1])=[O:10])[NH:8]1A solution of 15.8 g (0.1 mol) of N,N-dimethyl-2-(hydroxyimino)-3-oxobutanamide in 400 ml of ethanol and 100 ml of 2N hydrochloric acid over 2 g of catalyst (5% palladium on charcoal) is hydrogenated in a Paar shaker until 1 molar equivalent of hydrogen is taken up (3-5 hours). The catalyst is removed by filtration. A solution of 16.2 g (0.2 mol) of potassium cyanate in 80 ml of water is added, the solution is refluxed for 1 hour and concentrated until the product crystallizes. Recrystallization from 50% aqueous ethanol gives the title compound, m.p. 244°-246° C. (dec).
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