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1st October 2013 @ 09:40

A solution of 3-bromobenzenesulfonyl chloride (0.14 mL, 0.98 mmol, 1 equiv.) in THF (1.5 mL) was cooled to 0 ˚C. Dimethylamine (33% in abs. alcohol, 0.67 mL, 4.9 mmol) was added dropwise at 0 ˚C and the reaction mixture was stirred o/n whilst reaching room temperature. 

Reaction complete. EtOAc (5 mL) added and then 1M HCl (5 mL). Aqueous layers extracted with EtOAC (2 x 5 mL), then combined organic layers washed with water (5 mL), brine (5 mL), dried (MgSO4), filtered and evaporated to yield a pale oil that crystallised to a white crystal at the high vac.

Data: 

TLC 50:50 EtOAc/Hex - not briliant visualisation - need better system but no SM

AEW-89 and 90 (50-50 EtOAc:hex).jpg

1H NMR (200 MHz, CDCl3): δ 7.96–7.89 (1H, m), 7.79–7.67 (2H, m), 7.44 (1H, t, J 7.8), 2.74 (2H, s).

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Hazard and Risk Assessment:

See Synthesis of 3-bromo-N-methylbenzenesulfonamide (AEW 68-1) but with dimethylamine in abs. ethanol which is toxic by inhalation, in contact with skin and if swallowed. It is also highly flammable, and danger - poses danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed. Also poses risk of serious damage to eyes. 

InChi:

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

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Attached Files
AEW 89-1.png
AEW 89-1.cdx
AEW-89 and 90 (50-50 EtOAc:hex).jpg
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