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17th July 2017 @ 19:30
Scheme: [data]20948[/data] Products and Reactants: SM/P  (Z)-2-(4-chlorophenyl)-3-methoxy -3-phenylacrylonitrile  Guanidine chloride  Sodium methoxide  5-(4-chlorophenyl)- 6-phenylpyrimidine-2,4-diamine    mw  269.73  95.53  54.02  296.76   Equiv  1.00  3.00  3.00  1.00  mmol  0.489  1.47  1.47  0.489  g  0.132  0.140  0.079  0.145 mL           g/mL      1.059      Procedure: 7/12/17 Guanidine hydrochloride (0.140g,3 eq) and sodium methoxide (0.084g,3 eq) were dissolved in ethanol (1.05 mL) and stirred for 5 min. A solution of (Z)-2-(4-chlorophenyl)-3-methoxy-3-phenylacrylonitrile (1 eq) and ethanol (0.35 mL) was added to the cloudy, white solution. The reaction mixture was then  heated under reflux for 18 h.  7/13/17 The reaction mixture was diluted with dichloromethane. Saturated NaCl was added and the mixture was extracted three times with dichloromethane. Organic extracts were combined and dried over MgSO4. Solvent was removed under reduced pressure to yield a red/orange solid (0.064 g, 0.216 mmol, 44% yield).   7/14/17 Product was crystallized from methanol and placed in the freezer overnight.   7/17/2017 Recrystallization was reattempted.  Methanol was removed carefully with a pipette. Crystals were rinsed with ice-cold methanol and placed on high vac overnight (0.014g, .047 mmol, 10% yield). TLC: 7/13/2017  SM =2-(4-chlorophenyl)-3-methoxy-3-phenylacrylonitrile  Co  P = 5-(4-chlorophenyl)-6-phenylpyrimidine-2,4-diamine  10:90 EtOAc: Hexanes   [data]20954[/data] NMR Spectra: [data]20978[/data] The GC-MS showed an m+ peak approximately at 440 and an [m-15]+ peak at 425.  [data]21044[/data][data]21042[/data]  
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