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15th January 2014 @ 03:04
Reaction successful, product used in CT 5-1 Repeat of [blog=7989]Synthesis of 3-Bromo-N,N-dimethylbenzenesulfonamide (AEW 89-1)[/blog] on twice the scale Reaction scheme   Procedure A solution of 3-bromobenzenesulfonyl chloride (0.3 mL, 2.1 mmol) in THF (3 mL) was cooled to 0°C. Dimethylamine (33% in abs. alcohol, 1.8 mL, 10 mmol) was added dropwise at 0°C and the mixture stirred o/n whilst reaching room temperature.  The crude reaction mixture was diluted with water (10 mL) and extracted with ethyl acetate (3x10 mL). The organic layers were combined, washed with brine (10 mL), dried with magnesium sulfate and the solvent removed to yield a brown oil which crystallised when taken off the vacuum (590 mg).  Note: reaction was complete as analysed by TLC within 7 hours, however, insufficient time to work-up reaction by end of the day. Leaving the reaction mixture for longer does not seem to be a problem since it is normally run overnight. Also seems like extra starting material was added (using syringe) as yield >100% again. Data -TLC SM = 3-bromobenzenesulfonyl chloride, P = reaction mixture after mini work-up in EtOAc/water After 7 hours: 25% EtOAc/Hexane. Disappearance of starting material.  After overnight: 25% EtOAc/Hexane. Product does not seem to have degraded overnight.  -NMR 1H NMR of product after work-up. Spectrum is consistent with desired product according to AEW 89-1, suitable for use in the next reaction.  [data]8703[/data] Hazard and risk assessment [data]8643[/data] InchI strings InChI=1S/C6H4BrClO2S/c7-5-2-1-3-6(4-5)11(8,9)10/h1-4H  to InChI=1S/C8H10BrNO2S/c1-10(2)13(11,12)8-5-3-4-7(9)6-8/h3-6H,1-2H3
Attached Files
CT 4-1 scheme.cdx
CT 4-1 HIRAC.doc
CT 4-1 scheme.png
CT 4-1 HIRAC.pdf
CT 4-1 proton.pdf
CT 4-1.zip
CT 4-1 TLC 7h.JPG
CT 4-1 TLC overnight.JPG
Comments
Re: Synthesis of 3-Bromo-N,N-dimethylbenzenesulfonamide (CT 4-1) by Matthew Todd
27th January 2014 @ 09:47
What do the crystals look like, and does their melting point match the lit?