All Notebooks | Help | Support | About
17th July 2017 @ 19:30

Scheme:

Screen Shot 2017-07-17 at 2.34.05 PM.png

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,eq) and sodium methoxide (0.084g,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 eqand ethanol (0.35 mL) was added to the cloudy, white solution. Threaction 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  

    Screen Shot 2017-07-17 at 2.39.14 PM.png


NMR Spectra:

JS_LT_DaraprimBenzoylCrystals_PROTON_cdcl3_01.jpeg


The GC-MS showed an m+ peak approximately at 440 and an [m-15]peak at 425. 

dararpimbenzoylderretention.png
dararpimbenzoylderivitization.png

 

Attached Files
Screen Shot 2017-07-17 at 2.34.05 PM.png
Screen Shot 2017-07-17 at 2.39.14 PM.png
JS_LT_DaraprimBenzoylCrystals_PROTON_cdcl3_01.jpeg
dararpimbenzoylderivitization.png
dararpimbenzoylderretention.png