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28th January 2014 @ 22:35
Reaction successful with yield of 39 mg/43% Repeat of AT 6-4 with the original time of 6 hours to compare yield/purity with shorter times.  Reaction scheme Procedure AEW 99-1 (0.100 g, 0.4 mmol), isopropanol (3 mL) and ammonia (6 mL) were added to a sealed tube, stirred and heated at 120 °C for 6 hours. The solvent was removed under vacuum. The crude product was purified by flash column chromatography over silica (96:3.5:0.5 to 95:4.5:0.5 DCM/MeOH/NH3) to yield the product as a yellow solid (39 mg, 1.7 mmol, 42% ). Start time: 9:50 am Note: lower MeOH % than previous attempts (3.5% vs 4.5%) as products always eluted with overlap. However, still some overlap between fractions (see TLC data).  Data -TLC TLC of crude (P), co-spotted with product from CT 3-1 (R). Solvent 95:4.5:0.5 DCM/MeOH/NH3. Appears to have 2 major products, confirmed by 1H NMR below. TLC of column fractions. Still some overlap between the two major fractions (fraction 12) despite lower MeOH. Some fractions co-spotted with CT 3-1 as a reference (R) to check whether it is the desired product.  Fractions 13-18 were combined and dried. Fractions 8-11 were also combined for potential further analysis.  -NMR 1H NMR of crude product. Two products, appear to be the same as CT 3-2 (desired product and possibly the -OH product) and no starting material.  [data]9329[/data] 1H NMR of second fraction. Consistent with desired product, though small trace of other impurities.  [data]9413[/data] HIRAC [data]9111[/data] InChI strings InChI=1S/C6H2BrClN2S/c7-4-1-3-5(11-4)6(8)10-2-9-3/h1-2H to InChI=1S/C6H4BrN3S/c7-4-1-3-5(11-4)6(8)10-2-9-3/h1-2H,(H2,8,9,10)
Attached Files
CT 3-1 scheme.png
CT 3-1 HIRAC.pdf
CT 3-3 crude proton.pdf
CT 3-3 crude.zip
CT 3-3 column 3.JPG
CT 3-3 column 1.JPG
CT 3-3 column 2.JPG
CT 3-3 crude TLC.JPG
CT 3-3 column co-spot.JPG
CT 3-3 fraction 2.pdf
CT 3-3 fraction 2.zip