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30th September 2016 @ 02:39

 Started on 9/28

scheme

compound

MW (g/mol)

Mol (mmol)

g

Density (g/mL)

Volume (mL)

eqv

2 chloro 6 hydrazinylpyrazine

144.56

3.47

0.5084

 

 

1

toluene

 

 

 

 

15 mL

 

Triethyl orthoformate

148.20

6.94

1.22 g

0.891

1.14

2

TsOH

190.2

0.614

0.13g 

 

 

0.2

Product

 154.56

 3.47

 0.5136

 

 

 1

 

2-chloro-6-hydrazinylpyrazine (from Synthesis of 2-Chloro-6-hydrazinylpyrazine (MRLS 1-1) (0.5084 g, 3.47 mmol) was dissolved in dry toluene (15 mL). Dry Triethyl orthoformate (1.14 mL, 6.94 mmol) and TsOH (0.13g g, 10 mol %) were added, and the resulting reaction mixture was refluxed at 110 oC for 20 hours.

Procedure based on TM 37-14.

Log

9-27-16

Reaction was started at 3:00. 1-3 and triethyl orthoformate was added to toluene, but didn't dissolve until the toluene reaced about 60C. 

At about 3:45 once everything was dissolved, catalyst was added to prevent the insoluble black solid from forming (see HM1-5) 

9-28

11:00 am

A TLC was taken of the starting material, cospot, and reaction mixture. It showed very little starting material! This was in 60% etoac on sio2. 

Displaying FullSizeRender.jpg

The reaction was stopped, and the solvent removed under reduced pressure, resulting in a crusty black solid.

This solid was dissolved in DCM (quite soluble) and put into a Samplet (part of the biotage thing). The samplet was put into a dessicator to remove solvent, and then run on the biotage (settings: regular solvent ramp, 1.4L solvent, 50g KSIL column with samplet).

Fractions 33-67 contained the product, and the solvent was removed under reduced pressure. Pale yellow solid resulted. NMR done in DMSO. Proton NMR was great, 13C wasn't as good. GC/MS to come. 

Yield was 0.252g, 1.76mmol, for 50.4% yield. Bromination with NBS is the next step.

 

Attached Files
2-3postcolumnlabeled.pdf
2-3 carbon.pdf
MRLS_2-3dmso_29Sep_201601.zip