1H-1,2,4-Triazole → HCID 68781704, compound

HRID 2097970Notes

Reaction equation

HRID 2097970 reaction equation
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.Cl[C:7]1[S:8][CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13].CC(C)([O-])C.[K+]>CN(C=O)C.CCOCC>[N+:12]([C:11]1[CH:10]=[CH:9][S:8][C:7]=1[N:1]1[CH:5]=[N:4][CH:3]=[N:2]1)([O-:14])=[O:13]

Participants

6

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 2201862-Chloro-3-nitrothiopheneHCID 23665647Potassium tert-butoxide

Product 1

HCID 68781704HCID 68781704, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

1H-1,2,4-triazole (582 mg, 8.43 mmol), 2-chloro-3-nitrothiophene (1.15 g, 7.03 mmol) and potassium t-butoxide (944 mg, 8.43 mmol) were dissolved in DMF (30 mL). The resulting solution was stirred at 90° C. for 2 h, after which the reaction mixture was cooled to room temperature and diluted with Et2O. The solution was washed with brine and the organic phase was separated, dried (Na2SO4), filtered, concentrated under vacuum to give 1-(3-nitrothiophen-2-yl)-1H-1,2,4-triazole. Retention time (min)=1.073, method [1], MS (ESI) 197.0 (M+H).

Workup

  1. temperatureafter which the reaction mixture was cooled to room temperature
  2. washThe solution was washed with brine
  3. customthe organic phase was separated
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-d051de3c4296464e937524164c13c3eb
Source dataset
uspto-grants-2013_05
Patent number
US08450363B2

Reaction notes

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