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28th October 2014 @ 15:22

Reaction Scheme 


Experimental Procedure 

Compound 3 (0.2 g, 0.74 mmol) was treated with  Hydrazine hydrate - 64 % weight in H2O - (0.4 mL,  6 equivs) in EtOH (0.5 mL) . The resulting mixture was stirred overnight at reflux.

 

RISK ASSESSMENT 


JS 5-1.docx


InChI strings

InChI=1S/C12H8Cl2N2O/c13-8-3-1-4-9(7-8)15-12(17)10-5-2-6-11(14)16-10/h1-7H,(H,15,17)

to

InChI=1S/C12H11ClN4O/c13-8-3-1-4-9(7-8)15-12(18)10-5-2-6-11(16-10)17-14/h1-7H,14H2,(H,15,18)(H,16,17)

SMILES

ClC1=NC(C(NC2=CC=CC(Cl)=C2)=O)=CC=C1

to

O=C(NC1=CC=CC(Cl)=C1)C2=CC=CC(NN)=N2

 


Attached Files
23rd October 2014 @ 08:29

Reaction Scheme 

 

Procedure 

2,6-Dichloropyridine (Aldrich, 5 g, 33.75 mmol) was teated with neat Hydrazine hydrate - 64 % weight in H2O - (10 mL, 204 mmol) . The resulting mixture was stirred overnight at 60C. TLC analysis showed that little starting material had been formed. White crystals had crashed out of solution overnight - TLC revealed this to be starting material. EtOH (10 mL) was added to the solution to dissolve the starting material and the reaction was allowed to stir over the weekend at reflux. 

Upon removing from heat and then removing the solvents in vacuo the titled compound was generated.

Hazard & Risk Assessment

see Synthesis of 2-chloro-6-hydrazinylpyradine (JS 3-1)

JS 2-2.docx


InChI strings

InChI=1S/C5H3Cl2N/c6-4-2-1-3-5(7)8-4/h1-3H

to

InChI=1S/C5H6ClN3/c6-4-2-1-3-5(8-4)9-7/h1-3H,7H2,(H,8,9)

SMILES

ClC1=CC=CC(Cl)=N1

to

ClC1=CC=CC(NN)=N1

 NMR 

JS 4-1.pdf

Attached Files
23rd October 2014 @ 05:50


2-Chloropyrazine (1.8 g, 15.7 mmol) was dissolved in EtOH (15 mL), and hydrazine hydrate (1.6 mL, 31.4 mmol, 2 eq) added. The mixture was refluxed for 


Hazard and Risk Assessment:

See Preparation of 2-hydrazinylpyrazine (TM 62-1)

Strings:

InChI=1S/C4H3ClN2/c5-4-3-6-1-2-7-4/h1-3H

to

InChI=1S/C4H6N4/c5-8-4-3-6-1-2-7-4/h1-3H,5H2,(H,7,8)

 

ClC1=NC=CN=C1

to

NNC1=NC=CN=C1

Attached Files
22nd October 2014 @ 06:50

5-chloro-[1,2,4]triazolo[4,3-a]pyrazine (1 g, 6.5 mmol) was combined with N-bromosuccinimide (1.96 g, 7.2 mmol, 1.1 eq) in chloroform (50 mL), and refluxed from 4 pm.


N-bromosuccinamide was freshly purified by recrystalliation in water:

20 g in 200 mL, heated to 95 ˚C until all solid dissolved and then left to cool at rt until white crystals formed. Then cooled to 0 ˚C for 30 minutes, filtered washed with cold water to yield a white solid (15 g).

Hazard and Risk Assessment:

See Synthesis of 3-bromo-5-chloro-[1,2,4]triazolo[4,3-a]pyrazine (TM 57-1)

 

Strings:

InChI=1S/C5H3ClN4/c6-4-1-7-2-5-9-8-3-10(4)5/h1-3H

to

InChI=1S/C5H2BrClN4/c6-5-10-9-4-2-8-1-3(7)11(4)5/h1-2H

ClC1=CN=CC2=NN=CN21

to 

ClC1=CN=CC2=NN=C(Br)N21

Attached Files
21st October 2014 @ 00:24

 

Repeat of Synthesis of 2-Chloro-6-hydrazinylpyrazine (AEW 85-1), see also Synthesis of 2-Chloro-6-hydrazinylpyrazine (AEW 85-2) and Synthesis of 2-Chloro-6-hydrazinylpyrazine (AEW 85-3)

 

2,6-dichloropyrazine (21 g, 141 mmol) was dissolved in EtOH (100 mL), and hydrazine hydrate (13.5 mL, 270 mmol, 2 eq) added. The reaction mixture was stirred at reflux for 6 hours, 


The solvent was removed under reduced pressure to give a pale yellow solid. Water (~150 mL) and EtOAc (~200 mL) were added, and the mixture was shaken in an attempt to dissolve all solid. The organic layer was removed, the aqueous layer extracted with EtOAc (3 x 100 mL), and the combined organic layers washed with brine (~30 mL) before being concentrated under reduced pressure to yield 

 

Data:

Hazard and Risk Assessment:

See Synthesis of 2-Chloro-6-hydrazinylpyrazine (AEW 85-1)

InChi Strings:

InChI=1S/C4H2Cl2N2/c5-3-1-7-2-4(6)8-3/h1-2H

to

InChI=1S/C4H5ClN4/c5-3-1-7-2-4(8-3)9-6/h1-2H,6H2,(H,8,9)