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21st March 2012 @ 00:20
Product probably obtained. === Synthesis of aryl pyrrole primary amide from pyrrole acid chloride PMY 32-3 and gaseous ammonia. [b]Reaction Start Time: 15.40 21/03/12[/b] PMY 32-2 (98 mg, 0.39 mmol, 1 equiv.) was stirred in anhydrous THF (5 mL).[i]hexane switched to THF as the acid chloride was made into a stock solution before reaction for PMY 11-6.[/i] Anhydrous ammonia was bubbled through the solution for 5 minutes via a balloon. A pale precipitate forms leaving the reaction a milky suspension. After 1 hours, TLC shows reaction complete. The reaction was concentrated under a stream of nitrogen. The residue was stirred with DCM (20 mL) and water (10 mL) then separated. The aqueous was extracted once more with DCM (10 mL) and the combined organic extracts washed with brine then dried (MgSO4) and concentrated under reduced pressure to a pale yellow solid (94 mg, 104%). 1H NMR consistent with expected product but poorly shimmed. [b]TLC (66% EtOAc/hexane) visualised with UV and vanillin:[/b] [data]2062[/data] [b]NMR:[/b] [data]2092[/data][data]2090[/data] [b]See Also:[/b] [blog]2702[/blog] [b]Risk and Hazard Assessment:[/b] [data]2058[/data] [b]InChi:[/b] Starting Material: InChI=1S/C13H11ClFNO/c1-8-7-12(13(14)17)9(2)16(8)11-5-3-10(15)4-6-11/h3-7H,1-2H3 Product: InChI=1S/C13H13FN2O/c1-8-7-12(13(15)17)9(2)16(8)11-5-3-10(14)4-6-11/h3-7H,1-2H3,(H2,15,17)
Attached Files
TLC 1 hour
1H NMR crude
Re: Synthesis of pyrrole amide (PMY 42-1) by OSDD Malaria
25th January 2014 @ 01:49