Ethyl thiooxamate → 6-Amino-3-(2-methyl-3-nitrophenyl)-1,2,4-triazin-5(4H)-one

HRID 445917

Reaction equation

HRID 445917 reaction equation
[CH3:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4](=[NH:7])[NH:5][NH2:6].[NH2:15][C:16](=S)[C:17](OCC)=[O:18]>C(O)C>[NH2:15][C:16]1[C:17](=[O:18])[NH:7][C:4]([C:3]2[CH:8]=[CH:9][CH:10]=[C:11]([N+:12]([O-:14])=[O:13])[C:2]=2[CH3:1])=[N:5][N:6]=1

Participants

4

Reactant 2

HCID 2733398Ethyl thiooxamateHCID 178428718HCID 178428718, compound

Product 1

HCID 1359671086-Amino-3-(2-methyl-3-nitrophenyl)-1,2,4-triazin-5(4H)-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-methyl-3-nitrobenzimidohydrazide (2.10 g, 10.81 mmol) and ethyl 2-amino-2-thioxoacetate (3.60 g, 27.0 mmol) in ethanol (100 mL) was heated at reflux for 8 hr, during which period product precipitated. Upon cooling to rt, the product, 6-amino-3-(2-methyl-3-nitrophenyl)-1,2,4-triazin-5(2H)-one (2.18 g) was collected as a white solid by suction filtration and dried under vacuum. This product was 88% pure by HPLC. It was used in the next step without further purification.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 8 hr, during which period product
  3. customprecipitated
  4. filtrationthe product, 6-amino-3-(2-methyl-3-nitrophenyl)-1,2,4-triazin-5(2H)-one (2.18 g) was collected as a white solid by suction filtration
  5. customdried under vacuum
  6. customIt was used in the next step without further purification

Sources & evidence

ORD record
ord-78a07fd5ac114b1c9b59d3097d376b5c
Source dataset
uspto-grants-2013_07
Patent number
US08476430B2

Linked notes

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