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21st October 2014 @ 01:24

 

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)

20th October 2014 @ 06:23

AEW 174-1 (200 mg, 1.46 mmol, 1.00 equiv.) was  suspended in methanol (2 mL) and AcOH (0.05 mL). Aqueous formaldehyde (37% wt. 0.15 mL) added and stirred for 5 minutes. Sodium cyanoborohydride (92 mg, 1.46 mmol, 1.00 equiv.) was added portionwise. 

 

Data:

 

Hazard and Risk Assessment:

HIRAC AEW 188-1.pdf

 

InChi:

InChI=1S/C8H11NO/c9-8(6-10)7-4-2-1-3-5-7/h1-5,8,10H,6,9H2/t8-/m0/s1

to

InChI=1S/C9H13NO/c1-10-9(7-11)8-5-3-2-4-6-8/h2-6,9-11H,7H2,1H3


17th October 2014 @ 14:12

Reaction Scheme 

 

Procedure 

2,6-Dichloropyridine (Aldrich, 10 g, 67.5 mmol) was rreaced with neat Hydrazine hydrate - 35 % weight in H2O - (10 mL) . The resulting mixture was stirred overnight at room temperature. The following morning the solution was heated (to 90 O C bath temperature) for 1 hour and a TLC analysis was carried out using an ethyl acetate / hexane eluent (30 / 70 ) which showed that there was very little product formaion. However, a large amount of starting material was still present therefore the reaction was allowed to reflux over the weekend. 

 

Hazard & Risk Assessment


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

Attached Files
16th October 2014 @ 07:52

 

Reaction Scheme

Procedure

AEW 204-1 (3.69 mmol, 12.4 mmol) was stirred into CH2Cl2 (111 mL). PhI(OAc)(4 g, 612.4 mmol) was added and the resulting solution was stirred at room temperature.

 

Reference Spectra:

1H NMR, pure, DMSO, 300 MHz

JU 19-1 pure 300 MHz.pdf
 
JU 19-1 pure 13C 300 MHz.pdf
 
 

 

 

HIRAC

 See 5-chloro-3-(4-(difluoromethoxy)phenyl)-[1,2,4]triazolo[4,3-a]pyrazine (JU 19-1)

InChI strings

InChI=1S/C12H9ClF2N4O/c13-10-6-16-7-11(18-10)19-17-5-8-1-3-9(4-2-8)20-12(14)15/h1-7,12H,(H,18,19)/b17-5+

to

InChI=1S/C12H7ClF2N4O/c13-9-5-16-6-10-17-18-11(19(9)10)7-1-3-8(4-2-7)20-12(14)15/h1-6,12H

SMILES

ClC1=CN=CC(N/N=C/C2=CC=C(OC(F)F)C=C2)=N1

to

ClC1=CN=CC2=NN=C(C3=CC=C(OC(F)F)C=C3)N21

15th October 2014 @ 12:00

Reaction Scheme 

 

 

Procedure 

2,6-Dichloropyridine (Aldrich, 5 g, 33.75 mmol) was dissolved and stirred in ethanol (60 mL) to produce a clear solution .  Hydrazine hydrate - 35 % weight in H2O - (1.8 mL, 1.85 g, 37.12 mmol) was then added . The resulting mixture was heated at reflux (bath temperature 80-90˚C) for 18 hours . The solution was cooled and a TLC analysis was carried out using an ethyl acetate / hexane eluent (30 / 70 ) which showed that some product had been formed. However, a large amount of starting material was still present therefore the reaction was allowed to reflux again for 24 hours. 


Hazard & Risk Assessment


JS 2-1.doc


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


Attached Files