[OH-:1].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]#[N:12])=[CH:6][CH:5]=1.[CH3:13][NH:14][C:15](=O)[CH2:16]Cl>O>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:16][C:15](=[O:1])[N:14]([CH3:13])[C:11]2=[NH:12])=[CH:6][CH:5]=1In 25 ml. of water containing 0.84 g. of sodium hydroxide was dissolved in 3.2 g. of p-chlorophenylcyanamide. To the clear solution was added 2.25 g. of N-methylchloroacetamide. The reaction mixture was stirred for 48 hours at room temperature. The precipitate was filtered to yield 1.9 g. of product, m.p. 182°-184° C. After the initial product was filtered, the filtrate was left stirring another three days. An additional 1.2 g. of product precipitated from solution. Total yield of product was 3.1 g. (66%).
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