[CH3:1][N:2]([CH3:6])[C:3](=[S:5])[S-:4].C[NH2+]C.C=O.[CH3:12][C:13](=[O:18])[CH2:14][C:15](=[O:17])[CH3:16].[C:19](=S)=S>CO>[CH3:1][N:2]([CH3:6])[C:3](=[S:4])[S:5][CH2:19][C:14](=[C:13]([OH:18])[CH3:12])[C:15](=[O:17])[CH3:16]Dimethylammonium dimethyldithiocarbamate (33.2 grams, 0.20 mole), formaldehyde (16.2 grams of 37% aqueous solution, 0.20 mole), 2,4-pentanedione (20.0 grams, 0.20 mole), and carbon disulfide (15.2 grams, 0.20 mole) were dissolved in methanol (100 ml.). The temperature of the resulting reaction was kept below 27° C. with ice cooling. After three hours at 22° C.-29° C., the reaction mixture was cooled in ice and the precipitated product was filtered off, washed with cold methanol and water, and dried in air. The crude product, melting at 69.5° C.-71.5° C. (prior sintering) weighed 37.3 grams (80%). Repeated precipitation of the material from carbon tetrachloride solution by the addition of hexane gave pure 2-(1-hydroxyethylidene)-3-oxobutyl dimethyldithiocarbamate melting at 70° C.-72° C. The structure was determined from infrared and nuclear magnetic resonance spectra and elemental analysis.
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