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)

\frac{300mgComp1}{1}|\frac{1g}{1000mg}|\frac{1mol}{164.27g}=0.00183molComp1

Benzene

\frac{0.0143mmol}{24ml}|\frac{0.00183mol}{Xml}=3.07mlBenzene

Dimethylformamide (DMF)

Same as benzene (equivolume). 3.07ml DMF

2-chloro-3-nitropyridine (comp2)

Equimolar with comp1: \frac{Xg}{1}|\frac{1mol}{158.54g}=0.00183mol => Xg = 0.290g = 290mgComp2


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.


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