Identification | Back Directory | [Name]
3-chloropyrazine-2-carboxaMide | [CAS]
21279-62-9 | [Synonyms]
3-chloropyrazine-2-carboxaMide 3-Chloro-2-pyrazinecarboxaMide 2-Pyrazinecarboxamide, 3-chloro- 3-Chloro-pyrazine-2-carboxylic acid amide | [Molecular Formula]
C5H4ClN3O | [MDL Number]
MFCD09863915 | [MOL File]
21279-62-9.mol | [Molecular Weight]
157.558 |
Chemical Properties | Back Directory | [Melting point ]
187.0 to 191.0 °C | [storage temp. ]
under inert gas (nitrogen or Argon) at 2-8°C | [form ]
powder to crystal | [color ]
White to Orange to Green |
Hazard Information | Back Directory | [Synthesis]
Two methods for the synthesis of 3-chloropyrazine-2-carboxamide from 2-chloro-3-cyanopyrazine are described below:
The first method is based on the homolytic amidation reaction of 2-chloropyrazine, which is less effective. The procedure was as follows: 2-chloropyrazine (0.17 mol) was dissolved in formamide (3.7 mol), heated to 90 °C, and then ammonium peroxydisulfate (0.18 mol) was added in batches over a period of 1 hour. The reaction mixture was continued at 90 °C for 1 h, followed by standing for 24 h at room temperature. Upon completion of the reaction, the mixture was diluted with 100 mL of water, filtered, and the filtrate was continuously extracted with chloroform for 16 hours. A mixture of three positional isomers was obtained by rapid chromatography on silica gel stationary phase.
The second method used the partial hydrolysis reaction of 3-chloropyrazine-2-carbonitrile. The procedure was as follows: powdered 3-chloropyrazine-2-carbonitrile (0.104 mol) was slowly added to a mixture of concentrated hydrogen peroxide (0.95 mol) and water (195 mL) heated to 50 °C. The pH of the reaction mixture was adjusted to about 9 with 8% sodium hydroxide solution and the reaction temperature was maintained between 55 and 60°C. The reaction was stopped after 2.5 hours and cooled to 5°C. The precipitated crystals were collected by diafiltration and purified by recrystallization with ethanol. | [References]
[1] Molecules, 2014, vol. 19, # 7, p. 9318 - 9338 [2] Molecules, 2017, vol. 22, # 2, |
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