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9th July 2015 @ 01:04

Not using Ethanol as solvent, using only aqueous ammonia. (First attempt, TZ 1-1)

GitHub Issue #316


4rocedure:

2,6-dichloropyrazine (500 mg, 3.36 mmol, 1 eq) and ammona solution (6.7 mL, 0.50 M, 28% aqueous) were combined in a sealed tube. The reaction mixture was stirred at 100 degrees celcius for 18 hours. 

The reaction mixture was diluted with EtOAc (30 mL) and a saturated aqueous solution of sodium hydrogen carbonate (20 mL). The biphasic mixture was shaken in a separating funnel and then organic layers separated. Aqueous layers were washed with EtOAc (30 mL) and then combined organic layers were washed with brine (10 mL), dried (MgSO4), filtered and evaporated to give a pale yellow crystalline solid, which was dried in vacuo (290.1 mg, 67 % yield). No further purification, to be scaled-up on Monday.

Data:


TLC (EtOAc/petroleum benzine 50:50)

 crude NMR 300MHz, desired product with trace SM

TZ 1-2 crude 300 MHz.pdf
TZ 1-2 crude.zip

1H NMR (CDCl3 300 MHz): δ 7.91 (1H, s),  7.86 (1H, s), 4.71 (2H, bs).

See SM spectra (Synthesis of 6-chloropyrazin-2-amine (TZ 1-1))

Hazard and Risk Assessment:

 

HIRAC TZ 1-2.pdf

Literature:

http://worldwide.espacenet.com/publicationDetails/originalDocument?CC=WO&NR=2013068755A1&KC=A1&FT=D&ND=&date=20130516&DB=&&locale=en_EP

Strings:

ClC1=CN=CC(Cl)=N1

to

ClC1=CN=CC(N)=N1

 

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

to

InChI=1S/C4H4ClN3/c5-3-1-7-2-4(6)8-3/h1-2H,(H2,6,8)

Attached Files
HIRAC TZ 1-2.doc
HIRAC TZ 1-2.pdf
TZ 1-2.cdx
TZ 1-1 Target.png
TZ 1-2.png
TZ 1-2 crude.zip
TZ 1-2 crude.zip
TZ 1-2 crude 300 MHz.pdf