1H-1,2,4-Triazole → HCID 18380059, compound

HRID 2205907Notes

Reaction equation

HRID 2205907 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7](I)[CH:6]=[CH:5][C:3]=1[NH2:4].[NH:10]1[CH:14]=[N:13][CH:12]=[N:11]1>CN(C=O)C.C(OCC)(=O)C.[Cu](I)I>[Cl:1][C:2]1[CH:8]=[C:7]([N:10]2[CH:14]=[N:13][CH:12]=[N:11]2)[CH:6]=[CH:5][C:3]=1[NH2:4]

Participants

6

Reactant 2

HCID 92571H-1,2,4-TriazoleHCID 2829302-Chloro-4-iodoaniline

Product 1

HCID 18380059HCID 18380059, compoundYield 78%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Chloro-4-iodoaniline (2 g, 7.9 mmol), 1,2,4-triazole (0.62 g, 9 mmol) and copper iodide (0.15 g, 0.79 mmol) in DMF (10 ml) were heated to 140° C. and stirred under dry nitrogen for 72 hours. The reaction was cooled to room temperature and diluted with ethyl acetate (50 ml). The organic layer was washed with water, brine, dried over sodium sulfate and filtered. The solvent was removed under vacuum and the residue purified by silica gel column chromatography eluting with 20% ethyl acetate in dichloromethane to give the title compound as a white powder (1.2 g, 78%). 1H-NMR (500 MHz, CDCl3): δ 4.43 (s, 2H), 6.76 (d, J=8.7 Hz, 1H), 7.23 (dd, J=2.5 Hz, 8.6 Hz, 1H), 7.48 (d, J=2.4 Hz, 1H), 7.94 (s, 1H), 8.36 (s, 1H).

Workup

  1. washThe organic layer was washed with water, brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customThe solvent was removed under vacuum
  5. customthe residue purified by silica gel column chromatography
  6. washeluting with 20% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-c3545db79a4146f3ae869461f2ea8bb9
Source dataset
uspto-grants-2016_06
Patent number
US09371319B2

Reaction notes

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