User:Andrew W Long/Notebook/Synthesis of Lipid Modulators/2015/10/02: Difference between revisions
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== | ==Purification of Product of Rxn Between MTT and CNP, and Large-Scale Reaction Setup== | ||
* | Note that '''MTT''' refers to 5-(methylthio)-1,3,4-thiadiazole-2-thiol, and that '''CNP''' refers to 2-chloro-3-nitropyridine. Structures shown [[User:Andrew_W_Long/Notebook/Synthesis_of_Lipid_Modulators/2015/09/21#Reaction_of_5-.28methylthio.29-1.2C3.2C4-thiadiazole-2-thiol_.26_2-chloro-3-nitropyridine|here]] | ||
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'''Goals:''' | |||
*To purify the products of my second reaction (Ross carried it out with the modified procedure). | |||
*To set up a large-scale version of the previous small-scale reaction. Target compound must be synthesized and purified by Wednesday (10/07/15) | |||
'''Procedure for purification:''' | |||
#The product was shown to be slightly soluble in ethyl acetate (which is more polar than dichloromethane). The insoluble impurity could be the result of residual triethylamine. A "dirty column" was run in an attempt to remove the impurity. | |||
##The column was a Büchner funnel containing powdered silica, which sat in a vacuum flask. | |||
##The powdered silica was then made into a slurry with hexane. | |||
##The compound, once redissolved in methanol, was run through the column. It was hoped that the triethylamine would remain in the silica. | |||
##After the fraction collected with ethyl acetate was obtained, another flask was used to collect a methanol fraction. | |||
#Mass spectrometry was used to examine the two fractions. The result is shown below: | |||
XXX | |||
'''Procedure for large-scale rxn:''' | |||
#Calculations: | |||
##Start with mass of CNP and get moles of CNP: <math>\frac{250mg}{1}|\frac{1g}{1000mg}|\frac{1mol}{158.54g}=0.00158mol</math> | |||
##Get mass of MTT using moles of CNP (use 5% extra MTT since it is less valuable): <math>\frac{Xg}{1}|\frac{1mol}{164.27g}=1.05*0.00158mol=0.001659mol => X = 272.5mg</math> | |||
#Dump solids (CNP & MTT) into round bottom with stir bar. | |||
#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) | |||
#Put enough DMF to dissolve the solid into flask through one of the needle ports | |||
#Once dissolved, put 100-200mL triethylamine (TEA) into the reaction flask. | |||
#Allow to spin in mineral oil bath overnight on heat. | |||
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Revision as of 16:12, 5 October 2015
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Purification of Product of Rxn Between MTT and CNP, and Large-Scale Reaction SetupNote that MTT refers to 5-(methylthio)-1,3,4-thiadiazole-2-thiol, and that CNP refers to 2-chloro-3-nitropyridine. Structures shown here Goals:
Procedure for purification:
XXX Procedure for large-scale rxn:
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