1H-1,2,4-Triazole → HCID 10617092, compound

HRID 1957107Notes

Reaction equation

HRID 1957107 reaction equation
Br[CH2:2][C:3]1[C:12]([Cl:13])=[C:11]([Cl:14])[CH:10]=[C:9]2[C:4]=1[N:5]=[C:6]([O:18][CH2:19]C)[C:7]([O:15][CH2:16]C)=[N:8]2.[NH:21]1[CH:25]=[N:24][CH:23]=[N:22]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C(=O)C.C(OCC)(=O)C>[Cl:13][C:12]1[C:3]([CH2:2][N:21]2[CH:25]=[N:24][CH:23]=[N:22]2)=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:14])[N:8]=[C:7]([O:15][CH3:16])[C:6]([O:18][CH3:19])=[N:5]2

Participants

6

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 19068899HCID 19068899, compound

Product 1

HCID 10617092HCID 10617092, compoundYield 58.2%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 5-bromomethyl-6,7-dichloro-2,3-diethoxyquinoxaline (Preparation 1,176 mg, 0.5 mmol), 1,2,4-triazole (69 mg, 1.0 mmol) and anhydrous potassium carbonate (138 mg, 1.0 mmol) in dry N,N-dimethylacetamide (2 mL) was heated at 50° C. with stirring for 18 hours. The mixture was diluted with ethyl acetate, washed with water, and concentrated under reduced pressure. The residue was purified by flash chromatography using a hexane:ethyl acetate:methanol gradient to give 6,7-dichloro-2,3-dimethoxy-5-(1,2,4-triazol-1-ylmethyl)quinoxaline (99 mg, 58%).

Workup

  1. washwashed with water
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-9768fc2f6016405393cefbc3659044a3
Source dataset
uspto-grants-1998_07
Patent number
US05783572

Reaction notes

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