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18th January 2017 @ 21:32
[data]20499[/data] Reagents Equivalents Quantity  (mg / mL) mmol Molecular Weight g/mol 2-chloro-6-hydrazineylpyrazine 1 200 mg 1.38 mmol 144.56 2-(pyrrolidin-1-yl)benzaldehyde [NA-02-02-PURE] 1 240 mg 1.38 mmol 175.23 EtOH (proof.) - 9.6 mL 2.20 mmol   Procedure To a stirred solution of 200 proof EtOH (9.6 mL) 2-(pyrrolidin-1-yl)benzaldehyde (240 mg, 1.38 mmol, 1 eqv.) was diluted in a 50 mL RBF. This was followed by the addition of 2-chloro-6-hydrazineylpyrazine (200 mg, 1.38 mmol, 1 eqv.). The mixture was left to react for approx. three hours at room temperature while stirring. The reaction was monitored with the use of TLC analysis to check for completion-two plates. The reaction mixture [NA-03-01] (E)-2-chloro-6-(2-(2-(pyrrolidin-1-yl)benzylidene)hydrazineyl)pyrazine was later rotary evaporated and weighed (424.8 mg, 1.41 mmol, 102% yield). A sample of [NA-03-01] was obtained for 1H NMR analysis with the use of CDCl3 solvent and for TLC analysis (50% EtOAc/pet. Ether).   Notes: The mixture looked yellow orange at the beginning and gradually got darker till it became a maroon red at the end of experiment. At the start: [data]20618[/data]    [data]20616[/data]    [data]20620[/data]   Rotary evaporation of RM:  [data]20574[/data]   [data]20576[/data]     [data]20578[/data]     [data]20580[/data]   TLC PLATES (1) [data]20570[/data]        [data]20568[/data] (2) [data]20566[/data]        [data]20572[/data] Rf values of solution mixture: At 12:30 PM  Rf(1)= 0.63  -but too concentrated so done again Rf(2)= 0.61 – might have gone to completion  Rf value of product [NA-03-01] NMR sample:  Rf= 0.59   NMR [data]20552[/data]
Attached Files
Synthesis of NA-03-01.png
TLC NA-03-01 (2).JPG
TLC NA-03-01 (11).JPG
TLC NA-03-01 (1).JPG
TLC NA-03-01 (22).JPG