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21st May 2013 @ 04:41

Orange semi-solid (323 mg, 1.47 mmol, 83% crude yield)

AEW 58-1 Scheme

Procedure:

MNR 99-3 (300 mg, 1.76 mmol, 1 equiv.) was dissolved in N,N-dimethylethylenediamine (1.15 mL, 10.6 mmol, 6 equiv.) and stirred at 100 ˚C. AFter 1 h, no SM present on TLC although product couldn't be clearly seen either. Reaction mixture had turned from yellow solution to white/yellow cloudy mixture. Reaction was stopped and cooled to room temperature then partitioned between EtOAc and water. The aqueous phases were extracted with EtOAc (very cloudy white ppt started to form), then combined org. phases washed with brine, dried (MgSO4), filtered and evaporated to yield an orange oil.

AFter 1 h, no SM present on TLC although product couldn't be clearly seen either. Reaction mixture has turned from orange solution to white/yellow cloudy mixture. Reaction was stopped and cooled to room temperature then partitioned between EtOAc and water. The aqueous phases were extracted with EtOAc (insoluble white oil/solid started to crash out so all layers kept) then combined org. phases washed with brine, dried (MgSO4), filtered and evaporated to yield an orange oil, which slowly crystallised to an orange semi-solid (323 mg, 1.47 mmol, 83% crude yield) and used as crude in AEW 66-1. NMR shows impurity with similar signals to product - used without purification.

Data:

AEW 58-1 crude 1H.pdf
AEW 58-1 13 C.pdf

1H NMR (300 MHz, CDCl3) δ: 8.44 (1H, s), 7.62 (1H, d, J 5.7), 7.29 (1H, d, J 5.7), 3.83 (2H, t, J 6.7), 3.39 (3H, s), 2.84 (2H, t, J 6.7), 2.40 (3H, s), 2.19 (1H, s); 13C NMR (125 MHz, CDCl3) δ: 160.6, 158.3, 154.1, 131.4, 124.7, 114.0, 50.5, 49.6, 37.7, 36.3.

Hazard and Risk Assessment:

HIRAC AEW 58-1.pdf

InChi:

InChI=1S/C6H3ClN2S/c7-6-5-4(1-2-10-5)8-3-9-6/h1-3H

and

InChI=1S/C4H12N2/c1-6(2)4-3-5/h3-5H2,1-2H3

to 

InChI=1S/C10H14N4S/c1-14(2)5-4-11-10-9-8(3-6-15-9)12-7-13-10/h3,6-7H,4-5H2,1-2H3,(H,11,12,13)

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Attached Files
HIRAC AEW 58-1.pdf
AEW 58-1.png
AEW 58-1 13 C.pdf
aew 58-1 CRUDE.zip
AEW 58-1 crude 1H.pdf