2H-1,2,4-Triazole-3-carboxamide Chemical Properties

Melting point:

315 °C

Boiling point:

393.4±25.0 °C(Predicted)

Density 

1.537±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Aqueous Base (Slightly), DMSO (Slightly)

form 

Solid

pka

8.50±0.20(Predicted)

color 

White to Off-White

Major Application

pharmaceutical (small molecule)

InChI

1S/C3H4N4O/c4-2(8)3-5-1-6-7-3/h1H,(H2,4,8)(H,5,6,7)

InChIKey

ZEWJFUNFEABPGL-UHFFFAOYSA-N

SMILES

[nH]1ncnc1C(=O)N

CAS DataBase Reference

3641-08-5(CAS DataBase Reference)

Safety Information

HS Code 

2933999552

Storage Class

11 - Combustible Solids

2H-1,2,4-Triazole-3-carboxamide Usage And Synthesis

Uses

N-Des-1-β-D-ribofuranosyl Ribavirin (Ribavirin EP Impurity D) is an impurity in the synthesis of Ribavirin (R414475), a purine nucleoside analog; inhibits inosine monophosphate dehydrogenase (IMPDH). Used as an antiviral agent.This compound is suitable for pyruvate dehydrogenase (PDH) related research.

Definition

ChEBI: 1,2,4-triazole-3-carboxamide is a member of the class of triazoles that is 1H-1,2,4-triazole substituted by an aminocarbonyl group at position 3. It is the major catabolite and aglycon of ribavirin. It has a role as a human urinary metabolite and a drug metabolite. It is a member of triazoles, a primary carboxamide, a monocarboxylic acid amide and an aromatic amide.

Synthesis

GENERAL STEPS: Methylimine ethyl ester hydrochloride (34.5 g, 0.315 mol) and 100 mL of formamide were added to a 250 mL three-necked flask at room temperature, followed by the addition of sodium ethoxide (21.4 g, 0.315 mol) and stirred for 10 min. Next, 2-hydrazino-2-oxoacetamide (10.8 g, 0.105 mol) was added, and the reaction mixture was heated to 130 °C for 10 h. The reaction pressure was maintained at 10 MPa. The progress of the reaction was monitored by liquid chromatography, and the reaction was stopped after confirming the complete conversion of 2-hydrazino-2-oxoacetamide. After the reaction mixture was cooled to room temperature, the precipitated solid was collected by filtration, washed with water and dried. The final 1,2,4-triazolecarboxamide white solid 9.2 g was obtained in 78.2% yield.

References

[1] Patent: CN108794413, 2018, A. Location in patent: Page/Page column 4-6

2H-1,2,4-Triazole-3-carboxamide(3641-08-5)Related Product Information

• N-TERT-BUTYL-3-ISOPROPYL-5-OXO-4,5-DIHYDRO-1H-1,2,4-TRIAZOLE-1-CARBOXAMIDE
• 5-Amino-1-(3,5-dichloro-4-(4-chlorobenzoyl)benzyl)-1H-1,2,3-triazole-4-carboxamide
• N-TERT-BUTYL-3-(2-HYDROXYPROPAN-2-YL)-5-OXO-4,5-DIHYDRO-1H-1,2,4-TRIAZOLE-1-CARBOXAMIDE
• 5-METHYL-2-PHENYL-2H-1,2,3-TRIAZOLE-4-CARBOXAMIDE,5-METHYL-2-PHENYL-2H-1,2,3-TRIAZOLE-4-CARBOXAMIDE
• Rufinamide
• Ribavirin
• TARIBAVIRIN
• 1H-1,2,4-Triazole-3-carboxamide
• N-(2,4-DICHLOROPHENYL)-1-(2,4-DIFLUOROPHENYL)-5-METHYL-1H-1,2,4-TRIAZOLE-3-CARBOXAMIDE
• N-(3,4-DIFLUOROPHENYL)-5-METHYL-1-[3-(TRIFLUOROMETHYL)PHENYL]-1H-1,2,4-TRIAZOLE-3-CARBOXAMIDE
• 5-METHYL-N,1-BIS[3-(TRIFLUOROMETHYL)PHENYL]-1H-1,2,4-TRIAZOLE-3-CARBOXAMIDE,5-METHYL-N,1-BIS[3-(TRIFLUOROMETHYL)PHENYL]-1H-1,2,4-TRIAZOLE-3-CARBOXAMIDE
• 1-(2,4-DIFLUOROPHENYL)-5-METHYL-N-[3-(TRIFLUOROMETHYL)PHENYL]-1H-1,2,4-TRIAZOLE-3-CARBOXAMIDE
• N,1-BIS(4-CHLOROPHENYL)-5-METHYL-1H-1,2,4-TRIAZOLE-3-CARBOXAMIDE,N,1-BIS(4-CHLOROPHENYL)-5-METHYL-1H-1,2,4-TRIAZOLE-3-CARBOXAMIDE
• N,1-BIS(2,4-DIFLUOROPHENYL)-5-METHYL-1H-1,2,4-TRIAZOLE-3-CARBOXAMIDE,N,1-BIS(2,4-DIFLUOROPHENYL)-5-METHYL-1H-1,2,4-TRIAZOLE-3-CARBOXAMIDE
• 1-(2,4-DIFLUOROPHENYL)-N-(4-FLUOROPHENYL)-5-METHYL-1H-1,2,4-TRIAZOLE-3-CARBOXAMIDE
• 1-(4-CHLOROPHENYL)-5-METHYL-N-(4-METHYLPHENYL)-1H-1,2,4-TRIAZOLE-3-CARBOXAMIDE
• 1-(4-CHLOROPHENYL)-N-(4-METHOXYPHENYL)-5-METHYL-1H-1,2,4-TRIAZOLE-3-CARBOXAMIDE
• 1-(2,4-DIFLUOROPHENYL)-N-ISOPROPYL-5-METHYL-1H-1,2,4-TRIAZOLE-3-CARBOXAMIDE