User:Andrew W Long/Notebook/Synthesis of Lipid Modulators/2015/09/21

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Reaction of 5-(methylthio)-1,3,4-thiadiazole-2-thiol & 2-chloro-3-nitropyridine PART 1: Relevant Compounds 5-(methylthio)-1,3,4-thiadiazole-2-thiol (comp1) 2-chloro-3-nitropyridine (comp2) Desired product PART 2: Prelab Calculations 5-(methylthio)-1,3,4-thiadiazole-2-thiol (comp1) [math]\displaystyle{ \frac{300mgComp1}{1}|\frac{1g}{1000mg}|\frac{1mol}{164.27g}=0.00183molComp1 }[/math] Benzene [math]\displaystyle{ \frac{0.0143mmol}{24ml}|\frac{0.00183mol}{Xml}=3.07mlBenzene }[/math] Dimethylformamide (DMF) Same as benzene (equivolume). 3.07ml DMF 2-chloro-3-nitropyridine (comp2) Equimolar with comp1: [math]\displaystyle{ \frac{Xg}{1}|\frac{1mol}{158.54g}=0.00183mol =\gt Xg = 0.290g = 290mgComp2 }[/math] PART 3: Procedure Comp1 and a stir bar were added with benzene and DMF in a round bottom flask Flask was allowed to cool for 5min While stirring, sodium hydride (NaH) was added to the solution until the solution stopped producing bubbles After 15 minutes of stirring, comp2 was added to the reaction flask The flask was stirred at 80 degrees Celsius in a mineral oil bath for ~1hr Resulting solution was added to 100ml NH4Cl in a beaker The flask was washed with ethyl acetate (EtOAc) & also added to the NH4Cl A separatory funnel was used to extract the organic layer (upper layer) and siphon off the water layer A small sample of the solution (2-3 drops) was rotovapped and analyzed in the MS. No clear peaks indicating the presence of the desired product were identified on the positive or negative spectra The solution was rotovapped, dissolved in ethyl acetate, and bubbled with air overnight until dry PART 4: The Results The positive spectra from the gas chromatography mass spectrometer (GC-MS) The negative spectra from the gas chromatography mass spectrometer (GC-MS) As previously stated, neither of the spectra showed the clear presence of fragment peaks for the desired product of the synthesis.