21279-62-9|3-Chloropyrazine-2-carboxamide| Ambeed

Structure of 21279-62-9

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Quality Control of [ 21279-62-9 ] Purity: 98% SDS Specification

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Product Details of [ 21279-62-9 ]

CAS No. :	21279-62-9
Formula :	C₅H₄ClN₃O
M.W :	157.56
SMILES Code :	O=C(C1=NC=CN=C1Cl)N
MDL No. :	MFCD09863915
InChI Key :	YHPMRHPLAQSPHJ-UHFFFAOYSA-N
Pubchem ID :	301266

Safety of [ 21279-62-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 21279-62-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 21279-62-9 ]
Downstream synthetic route of [ 21279-62-9 ]

[ 21279-62-9 ] Synthesis Path-Upstream 1~4

1
[ 55557-52-3 ]
[ 21279-62-9 ]

Yield	Reaction Conditions	Operation in experiment
80%	With dihydrogen peroxide; sodium hydroxide In water at 50 - 60℃; for 2.5 h;	The starting compound 3-chloropyrazine-2-carboxamide was synthesized using two published procedures. The first method was classified as less effective and was based on the homolytic amidation of 2-chloropyrazine. Thus, 2-chloropyrazine (0.17 mol) was dissolved in formamide (3.7 mol), heated to 90 °C and ammonium peroxodisulphate (0.18 mol) was added portionwise over one hour period. This mixture reacted for another one hour at 90 °C and then it was left to stand for 24 h at laboratory temperature. Dilution with 100 mL of water was followed by filtration and this filtrate was extracted continuously with chloroform for 16 h [34,42]. The mixture of three positional isomers was separated by flash chromatography using silica gel as stationary phase. The second process used 3-chloropyrazine-2-carbonitrile, which was submitted to partial hydrolysis of the nitrile group. The powdered carbonitrile (0.104 mol) was added little by little into the reaction mixture of concentrated hydrogen peroxide (0.95 mol) and water (195 mL) heated to 50 °C. The pH was adjusted and regulated around a value of 9 using an 8percent solution of sodium hydroxide and the temperature of the reaction was regulated between 55 and 60 °C. The reaction was stopped after 2.5 h and was cooled to 5 °C. Newly-emerged crystals were removed by suction and recrystallized from ethanol [42].
80%	at 50 - 55℃; for 3 h;	The starting compound 3-chloropyrazine-2-carboxamide was prepared via partial hydrolysis of the nitrile group of 3-chloropyrazine-2-carbonitrile (Fluorochem, Co., Hadfield, Derbyshire, UK). A mixture of concentrated (30percent) hydrogen peroxide (29 mL) and water (195 mL) was prepared and alkalinized with an 8percent (w/v) solution of sodium hydroxide to obtain a solution with pH 9. The carbonitrile (104 mmol) was then added portionwise into the heated (50 °C) mixture over a period of 30 min. The whole mass was stirred for an additional 2.5 h at 55 °C while the pH was periodically monitored and alternatively adjusted to the value of 9 by adding a few drops of 8percent NaOH solution. The reaction mixture was cooled in a fridge to initiate crystallization. The crude product was recrystallized from ethanol [27]. The yield of this reaction was approximately 80percent.

References: [1] Molecules, 2014, vol. 19, # 7, p. 9318 - 9338.
[2] Molecules, 2017, vol. 22, # 2, .

2
[ 14508-49-7 ]
[ 77287-34-4 ]
[ 21279-62-9 ]

Yield	Reaction Conditions	Operation in experiment
25%	at 90℃; for 26 h;	The starting compound 3-chloropyrazine-2-carboxamide was synthesized using two published procedures. The first method was classified as less effective and was based on the homolytic amidation of 2-chloropyrazine. Thus, 2-chloropyrazine (0.17 mol) was dissolved in formamide (3.7 mol), heated to 90 °C and ammonium peroxodisulphate (0.18 mol) was added portionwise over one hour period. This mixture reacted for another one hour at 90 °C and then it was left to stand for 24 h at laboratory temperature. Dilution with 100 mL of water was followed by filtration and this filtrate was extracted continuously with chloroform for 16 h [34,42]. The mixture of three positional isomers was separated by flash chromatography using silica gel as stationary phase. The second process used 3-chloropyrazine-2-carbonitrile, which was submitted to partial hydrolysis of the nitrile group. The powdered carbonitrile (0.104 mol) was added little by little into the reaction mixture of concentrated hydrogen peroxide (0.95 mol) and water (195 mL) heated to 50 °C. The pH was adjusted and regulated around a value of 9 using an 8percent solution of sodium hydroxide and the temperature of the reaction was regulated between 55 and 60 °C. The reaction was stopped after 2.5 h and was cooled to 5 °C. Newly-emerged crystals were removed by suction and recrystallized from ethanol [42].

References: [1] Molecules, 2014, vol. 19, # 7, p. 9318 - 9338.

3
[ 14508-49-7 ]
[ 77287-34-4 ]
[ 21279-62-9 ]
[ 36070-79-8 ]
[ 21279-64-1 ]

References: [1] Collection of Czechoslovak Chemical Communications, 1990, vol. 55, # 10, p. 2493 - 2501.
[2] Collection of Czechoslovak Chemical Communications, 1990, vol. 55, # 10, p. 2493 - 2501.

4
[ 27825-21-4 ]
[ 21279-62-9 ]

References: [1] Journal of the Chemical Society, 1956, p. 2066,2070.

[ 21279-62-9 ] Synthesis Path-Downstream 1~35

1
[ 21279-62-9 ]
[ 74-89-5 ]
[ 98135-38-7 ]

Yield	Reaction Conditions	Operation in experiment
61.4%	With pyridine; In methanol; at 140℃; for 0.5h;Microwave irradiation;	General procedure: The starting compound (1.27 mmol) was treated with 18 aliphatic amines, alicyclic amines or saturated heterocycles containing at least one nitrogen atom (2.54 mmol). Four reactions were completed by conventional heating methods. The conditions were 110 C, toluene as a solvent and pyridine (1.27 mmol) as a base. The reaction time was set to one hour. Then the reactions were completed using the microwave reactor with focused field and conditions used for syntheses were 140 C, 30 min,120 W, methanol used as a solvent and pyridine (1.27 mmol) as a base. They were set experimentally with respect to prior experience. The progress of reaction was monitored with TLC in system hexane/ethyl acetate (1:1). Then the mixture was separated by flash column chromatograph using gradient elution. Mobile phases were hexane and ethyl acetate again.

References: [1]Molecules,2014,vol. 19,p. 9318 - 9338.
[2]Journal of the Chemical Society,1956,p. 2066,2070.

2
[ 27825-21-4 ]
[ 21279-62-9 ]

References: [1]Journal of the Chemical Society,1956,p. 2066,2070.

3
[ 14508-49-7 ]
[ 77287-34-4 ]
[ 21279-62-9 ]
[ 36070-79-8 ]
[ 21279-64-1 ]

References: [1]Collection of Czechoslovak Chemical Communications,1990,vol. 55,p. 2493 - 2501.
[2]Collection of Czechoslovak Chemical Communications,1990,vol. 55,p. 2493 - 2501.

4
[ 21279-62-9 ]
[ 131295-39-1 ]

References: [1]Collection of Czechoslovak Chemical Communications,1990,vol. 55,p. 2493 - 2501.

5
[ 21279-62-9 ]
[ 132274-87-4 ]

References: [1]Collection of Czechoslovak Chemical Communications,1990,vol. 55,p. 2493 - 2501.

6
[ 21279-62-9 ]
[ 24851-67-0 ]

References: [1]Journal of the Chemical Society,1956,p. 2066,2070.

7
[ 21279-62-9 ]
[ 75-04-7 ]
3-(ethylamino)pyrazine-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78.7%	With pyridine; In methanol; at 140℃; for 0.5h;Microwave irradiation;	General procedure: The starting compound (1.27 mmol) was treated with 18 aliphatic amines, alicyclic amines or saturated heterocycles containing at least one nitrogen atom (2.54 mmol). Four reactions were completed by conventional heating methods. The conditions were 110 C, toluene as a solvent and pyridine (1.27 mmol) as a base. The reaction time was set to one hour. Then the reactions were completed using the microwave reactor with focused field and conditions used for syntheses were 140 C, 30 min,120 W, methanol used as a solvent and pyridine (1.27 mmol) as a base. They were set experimentally with respect to prior experience. The progress of reaction was monitored with TLC in system hexane/ethyl acetate (1:1). Then the mixture was separated by flash column chromatograph using gradient elution. Mobile phases were hexane and ethyl acetate again.