User:Andrew W Long/Notebook/Synthesis of Lipid Modulators/2015/10/19

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Beginning AL2, 500mg scale

Reaction summary

This reaction is being done with 4-nitrobenzenethiol (NBT) (aka 4-nitrothiophenol) and 2-chloro-3-nitropyridine (CNP).


  • molar mass of NBT = 155.17 g/mol
  • molar mass of CNP = 158.54 g/mol
  • Start with mass of CNP and get moles of CNP:

\frac{250mg}{1}|\frac{1g}{1000mg}|\frac{1mol}{158.54g}=0.00158mol Actual mass used: 253mg

  • Get mass of NBT using moles of CNP:

\frac{Xg}{1}|\frac{1mol}{155.17g}=0.00158mol => X = 0.245g = 245mg Actual mass used: 244mg


  1. Dump solids (CNP & NBT) into round bottom with stir bar.
  2. Evacuate the flask with nitrogen gas (put a septum on the opening, wrap in parafilm, stick two needles through the septum, connect one of the needles to the nitrogen tank output, wait ~2min, disconnect the nitrogen tank and shut it off)
  3. Put enough DMF to dissolve the solid into flask through one of the needle ports
  4. Once dissolved, put 100-200mL triethylamine (TEA) into the reaction flask (I used ~150mL).
  5. Allow to spin in mineral oil bath overnight on heat.

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