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description=2 posts published by milkshake during October 2010;

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october, 2010, org, prep, daily, 25, diaminotriazoles, from, anilines, mercaptooxindole,

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october 2010 org prep daily org prep daily october 25 2010 diaminotriazoles from anilines filed under procedures milkshake 3 04 pm dimethylamide of p aminobenzoic acid 6 00g 36 54 mmol and pho 2c n cn 10 14g aldrich 42 56 mmol in anhydrous thf 60ml was refluxed under nitrogen on a 80c oil bath for 2 days note 1 the cooled reaction mixture was concentrated on rotovap the obtained oily residue was diluted with anh thf 20ml and cooled to 0c anhydrous hydrazine 1m solution in thf 60ml aldrich was added the mixture was stirred on ice for 15 min and at ambient temperature for 20 min then placed on a 70c oil bath and refluxed under nitrogen for 30 min the reaction mixture was cooled to room temperature the precipitated product was collected by filtration and washed with mtbe tbuome then dried by suction and on highvac y 10 48g of a white fluffy powder 90 th as a 1 1 solvate with thf 1h d6 dmso 400mhz 11 22 br s 1h 8 94 br s 1h 7 52 app d 8 6hz 2h 7 27 app d 8 6hz 2h 5 92 br s 2h 3 60 m 4h thf 2 95 s 6h 1 76 m 4h thf 13c d6 dmso 100mhz 170 47 128 29 114 44 67 00 thf 25 11 thf note 1 1 day reflux would have been enough note 2 the starting aniline was prepared by hydrogenation of dimethylamide of p nitrobenzoic acid 5 pt c h2 baloon etoac which was obtained from p nitrobenzoyl chloride and 40 aq dimethylamine in thf at 15 c the yield was 90 over two steps comments 14 october 6 2010 5 mercaptooxindole filed under procedures milkshake 2 51 pm chlorosulfonic acid 115 ml 1 73 mol in a 1l wide mouth round flask with a 45 50 joint equipped with a gas outlet tube was cooled on ice bath and solid oxindole 25 60g 192 2 mmol was gradually spooned in with vigorous stirring and cooling on ice over a 20 min period a corrosive fog evolution after the complete addition the flask was removed from the cooling bath and the mixture was stirred for additional 15 min the flask was then placed on a 70c oil bath and the mixture was stirred at 70c for 2 hours the resulting dark reaction mix was cooled on ice then very cautiously poured in a thin stream onto crushed ice 1 4kg that was pre chilled in a freezer in a 3l beaker with stirring note 1 the quenched mixture was stirred until all ice melted the precipitated solid was collected by filtration on a very large glass buchner funnel washed with 0 05 m hcl semi dried by filtration and then carefully dried on highvac note 2 y 42 23g 95 th of a tan solid the sulfonylchloride from the previous step 42 23g 182 3 mmol was suspended in anhydrous dichloromethane 100ml in a 1l round flask the mixture was cooled on ice slush bath and a solution of triphenylphosphine 167 5g 638 mmol 3 5 eq in anhydrous dichloromethane 300ml was dropwise added from an addition funnel under nitrogen with cooling over a 45 min period after complete addition the flask was removed from the cooling bath and the mixture was stirred at room temperature for 3 hours the reaction was quenched by water addition 200ml the flask with the biphasic mixture was placed on a 50c water bath and the mixture was refluxed under nitrogen for 1 hour then cooled on ice the precipitated product was collected by filtration washed thoroughly with ice chilled dichloromethane and ice water then dried by suction and on highvac to provide 19 58g of a pure product the biphasic filtrates were de oxygenated by argon vacuum purge 3 times the mixture was made strongly alkaline by addition of 50 aq naoh solution shaken under ar and then rapidly separated the organic phase was re extrated with water note 3 the aqueous phases were promptly washed with fresh dichloromethane 200ml the combined aqueous extracts were made acidic by addition of 6m hcl the mixture was cooled on ice the precipitated product was collected by filtration washed with ice cold water dried by suction and on higvac to provide a second crop of the product 7 15g the combined yield was 26 73g 88 5 th of a light tan solid 1h d6 dmso 400mhz 10 339 s 1h 7 151 s 1h 7 108 m 1h 6 707 d 8 0hz 1h 5 109 s 1h 3 436 s 2h note 1 chlorosulfonic acid is viciously corrosive and has a huge quench exotherm the quench has to be done in a fume hood with the sash pulled down and a full protection as there is a good chance of the reaction mixture splashing out plain latex gloves are no match for clso3h use thick long sleeved ones note 2 wet chlorosulfonyl oxindole has thixotropic properties a wet solid that suddenly starts flowing as a sludge when shocked this is not a sign of decomposition the wet sulfonyl chloride after filtration was transferred into a glass dish and thoroughly dried on highvac drying this quantity of material took 2 days over weekend a thoroughly dry sulfonyl chloride is required for the success of the next step incomplete drying or substituting anhydrous dcm for a non anhydrous dcm grade stabilized with methanol 0 5 resulted in a product containing a large quantity of the corresponding symmetric disulfide note 3 the product is soluble in aqueous naoh as a thiolate the alkaline solutions will gradually oxidize on air to the disufide but the extraction can be actually done without a protective atmosphere if one works without delay comments 31 pages about milkshake about org prep daily bug report chemistry resources chemistry chemjobber in the pipeline med chemist open flask org chem portal practical fragments stellen fuer chemiker edible links serious eats links to behold idle words categories chris douglas industry life krest17 lab destruction lit highlights mechanisms procedures questions uncategorized search archives january 2026 december 2025 november 2025 october 2025 september 2025 april 2019 march 2019 december 2018 june 2018 september 2017 august 2017 march 2016 october 2015 august 2015 july 2015 june 2015 march 2015 november 2014 july 2014 may 2014 september 2013 july 2013 may 2013 april 2013 october 2012 september 2012 august 2012 january 2012 december 2011 november 2011 october 2011 july 2011 june 2011 april 2011 december 2010 november 2010 october 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