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10th December 2016 @ 05:28
New: New

Reaction run on 12/8/16

CC1=NC(C)=C(N=C1Cl)N/N=C/C2=CC=C(OC(F)F)C=C2

Procedure:

4-(difluoromethoxy) benzaldehyde (1.5 mL) was added to 2-chloro-6-hydrazineyl-3,5-dimethylpyrazine (0.8g) in a 50 mL round bottom flask. Ethanol (20 mL) was added to the flask with vigorous stirring. The honey mustard product was left overnight at room temperature. TLC was run on the product to determine completion and presence of desired product. The product was then vacuum filtered resulting in 1.4g of a dried yellow powder. Yield: 1.4/1.10 = 127%


Attached Files
10th December 2016 @ 05:11
New: New

Reaction taken place on 12/5

CC1=NC(C)=C(N=C1Cl)NN

Procedure:

2,6 dichloro-3,5 dimethylpyrazine (0.6g), ethanol (6mL) and hydrazine (0.15 mL) were combined in a round bottom flask and stirred under argon atmosphere. It was then heated in an 80oC oil bath overnight. After, the solvent will be removed under vacuum. Yellow/gold crystals (0.8g) resulted NMR shown below.

 


10th December 2016 @ 05:06
New: New

Columned on 11/28/16

The product was columned by the Biotage. The fractions 5-7 (high spots) were combined. The product was a white crystal. Fractions 19-30 were also combined (low spot). NMR was run on the high spot. Initial look suggests that the chlorinated dimethyl product was synthesized with traces of starting material. Ran NMR/GCMS on both high and low spots, shown below.

 

Silica gel plates. 50/50 EtoAc/Hexane. Active under UV light.


10th December 2016 @ 04:57
New: New

Date of Reaction: 11/23

CC1=NC(C)=C(N=C1Cl)Cl

 

Procedure:

Excess phosphoryl chloride (5.0mL, 0.0535 mol) was added to the oxidized dimethyl product (1.2g, 0.008 mol). The mixture was stirred and refluxed for 1.5 hours at 70oC. The reaction mixture was then alkalized using 20% NaOH. An extraction was carried out with CHCl3 (3 x 20 mL). Next steps will be to run a column chromatography on that product and then to get NMR data.

 

Table of Reagents (Rxn2) DiMethyl

 
 
 
 
 

Reagent

mass (g)

mols

Molecular Weight (g/mol)

Volume (mL)

Density (g/mL)

Product RxN1

1.200

0.008

158.590

 
 

Phosphoryl Chloride

3.481

0.023

153.333

2.122

1.640

Product RxN2 Dimethyl

1.347

0.008

178.040

 
 
 
 
 
 

*Used 5 mL of POCl3

 

Attached are TLCs 

Attached Files
7th December 2016 @ 19:43
New: 1

CC1=NC(C)=C(Cl)[N+]([O-])=C1

ImageIMG_9860.JPG

SM/P 

2-chloro-3,5-dimethylpyrazine 

sulfuric acid, conc. 

potassium persulfate 

2-chloro-3,5-dimethylpyrazine 1-oxide 

mw 

142.59 

  

270.31 

158.59 

Equiv 

1.00 

  

1.07 

1.00 

mmol 

14.00 

  

15.00 

14.00 

mg 

2000 

  

4000 

2220 

mL 

  

14.00 

  

  

11/8/2016.  To a 1-neck 14/20 50 mL RB were added 14 mL of concentrated H2SO4, which was cooled to approximately 0 C with ice bath.  The pyrazine was then added, followed by potassium persulfate.  The resulting suspension was allowed to stir with warming to room temperature overnight. 

11/9/16.  The resulting clear solution was poured into a separatory funnel with distilled water and ice and extracted 3 x ~ 90 mL CHCl3.  The combined organic layer was washed with saturated aqueous NaHCO3, water, and brine and dried over MgSO4

11/13/16.  The resulting clear, colorless solution was concentrated with rotary evaporation to afford 2.5 g of a clear, colorless liquid from which a colorless solid formed upon cooling. 

11/14/16.  The Round bottom flask was placed under high vacuum for approximately 1-1.5 hours to afford 1.9 g of a colorless crystalline solid after removal of high vacuum volatiles.  

Crude yield 1900/2200 x 100 = 86%