Make p-Chlorophenyl Acetonitrile - Step 4 in Pyrimethamine Synthesis | Tokyo
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In this video we make p-chlorophenyl acetonitrile from the p-chlorobenzyl chloride and the sodium cyanide in a previous video. ( Complete pyrimethamine playlist so far: https://www.youtube.com/playlist?list=PLU79801KtVAU1XsTwHaKkqQoBgz_VYmPS ) Fortunately this is a very mild process and doesn't need exotic conditions like ultraviolet light or high temperatures. We reflux together 7.2g of potassium iodide, 19g of sodium cyanide, 50g of p-chlorobenzyl chloride and 250mL of dry acetone for at least one full day. What happens is the iodide replaces the benzylic chloride on the p-chlorobenzyl chloride in a reaction known as the Finkelstein reaction. This highly reactive p-chlorobenzyl iodide now reacts with sodium cyanide to form p-chlorobenzyl cyanide, or p-chlorophenyl acetonitrile. To recover it, first filter the salts from the acetone solution. The salts should be destroyed with an oxidant to render the sodium cyanide harmless. The filtrate is distilled to remove acetone. The residue is washed with 150mL water and 15g sodium metabisulfite solution. the denser organic phase is extracted off and washed again. the organic phase now consists mostly of p-chlorophenyl acetonitrile with some p-chlorobenzyl amine as the next most significant impurity. Donate to NurdRage! Through Patreon (preferred): https://www.patreon.com/NurdRage Through Bitcoin: 1NurdRAge7PNR4ULrbrpcYvc9RC4LDp9pS Glassware generously provided by http://www.alchemylabsupply.com/ Use the discount code "nurdrage" for a 5% discount. Social media links: Twitter: https://twitter.com/NurdRage Facebook: https://www.facebook.com/NurdRageYoutube/ Instagram: https://www.instagram.com/nurdrageyoutube/ This video generously sponsored by my patrons: Jon Stanovich Michael Zappe Emil Mikulic Alex S. My P. Nis Lord Martin Hill Matthew Brunette Simon Bitdiddle Cullen Purkis Carl Potter Zane Bacon Roger Martel DuVigneaud Bryan Boettcher Dror Kronstein Michael Gregg Robert Boll Nick Kinnan doug dysart william tips Daniel Astbury Shutaro Highwind Stephen Stair Bobby Nansel Andrea Nall Dom Vasta Tyler Bushey Michael Syam Krishnan Mark Rose Phillip Hutchings Uocjat Marius Klimantavičius Dino Capiaghi Henry Wu steve Antton Tapani Evan Schuld Mecha Chocobo Jason King David Gilmour Dean Bailey Matt Sieker Ben Anderson Jeremy Porter Chase Curtis Connor Reed Wolf Bennett Christian Cooper Samuel Pelzer Wesley Gardner Gabriel Jeantelot Kremling Brian Nietfeld Jean-Marc Bélisle Leon Verrall Feliksas Egan Loughran George Jefferies Syniurge evan Applied Science Micha Gorelick Hanna Anderberg Marcio Yukio Teruya Timothy Vincent Chris M Guerra Patrick Sweetman Collin B Douglas Daniel L. Michal Z Florent Parent Thor Danny Chan Miguel-Angel Gutierrez Casey Kikendall David Drueding Kay Bærulfsen Adrian Kleven Mark Beeunas David Craig House John Bonnin Triple Cee Rauni Kangas Daniel Åland Stephen Andrew Montagne Lior Z.L Joshua L Digiacomo Samuel Ytterbrink Tristan Putzeys Randi Silva Ed McMullen nBoost Output Coupler Xandorcode Al Longley Ariesticnig Greg Emmons Woobly Mark L Pascal De Lisio Tazobactam Emil Lund Jonathan Bear Joshua Crager Rebecca Chung Zach Schneider cj6xu6ru Johann Massyn Goodwine Meyer Bill Noren Joshua Books OpenArms Jason Brammer Paul Grodt Mark Keibler Bas Hessels Joshua Rogers upsidedownoj Julian Nicolai Herbert999 Myndert Papenhuyzen Dean Leggo Tyler Faruque Ross Clark Damien P Kevin C Akshay Joshi Rob Parker Robin Beckett James McIlhargey LVE LFTRnow Magnus Ott Kartin Marc Ethier rd Bob Drucker Kelvin Sac LeGaie Aner Nitsan Donald W Ricardo Hy Diep John Wasser Jeffrey Morse Braxton Thomason Åsmund Tveten CNK054so Essimage Marius Grey Shot Leonard Marshall jMe4505 Timothy Glore
Comments
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I've always wondered why chemists use foil to insulate distillations. Wouldn't the aluminum conduct heat from the glass air since aluminum has a high thermal conductivity? Why not use other material such as glass wool since glass wool is an extremely good insulator and does not catch fire/decompose at high temperatures?
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I like boobs
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Thanks for the pathway graphic, it really helps put the video in context of the whole synthesis. :)
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Very cool! I've really enjoyed following your saga towards pyrimethamine.
I've been wondering for a while now why you don't use TLC to check for purity and column chromatography to purify your product. Is there a particular reason, or do you simply prefer purifying by distillation and crystallization? -
Nerd Rage,
I am not a scientist. At best, I am an amateur astronomer. I however enjoy watching your videos. Thank you for making them. Take care. -
Description says sodium iodide instead of sodium cyanide.
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hmmm organic chemistry blows my mind . nurdrage just a question , this whole process is it industrially viable , what i mean by that is the process that you use , can it be modified for major production . anyone else can also answer . curiosity overwhelms me .
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i took freshmen chemistry lab in college and had a REALLY good high school teacher but i seem to have forgotten everything because 2 mins in and im 90% sure you pulling a star trek on me and making shit up still fun to watch though :)
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First year Chem student here. I really appreciate you putting the NMR spectroscopy results in this video. Happy Holidays!
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why couldn't the p-chlorobenzyl chloride react with the cyanide without the catalyst?
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I'm sure it has been asked, but what are the costs associated with getting those NMR test results?
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Do you have a script you read from that you have previously wrote or could you just narrate this live? What you do is fascinating! I envy your knowledge.
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you could make a video on how to make sodium hydroxide from wood and then maybe making sodium bicarbonate from that letting it react with CO2 from air
unfully burnt wood dumped in water somehow gives off caustic soda, all about the basic chemicals -
8:30 Is that weak splitting of the benzyl protons from Nitrogen-15?
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Would you be interested in making formaldehyde? I'm looking to make stove pellets from hexamethylenetetramine. or if there would be easily obtained precursor to make hmx.
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What is the stirring bar made of?
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+NurdRage
How much the NMR spectroscopy cost? What lab you are using? -
Please do make the video of the cyanide purification and titration. I do enjoy these videos.
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wrap in foil to keep in the heat? it might stop convection directly next to the glass but wouldnt it also act like a heatsync?