Dimethylformamide → HCID 67047909, compound

HRID 606331Notes

Reaction equation

HRID 606331 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)C=O.[N:12]1([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)[CH:16]=[N:15][CH:14]=[N:13]1.Br[C:25]1[CH:26]=[CH:27][C:28]([N+:31]([O-:33])=[O:32])=[N:29][CH:30]=1>O>[N+:31]([C:28]1[CH:27]=[CH:26][C:25]([O:23][C:20]2[CH:19]=[CH:18][C:17]([N:12]3[CH:16]=[N:15][CH:14]=[N:13]3)=[CH:22][CH:21]=2)=[CH:30][N:29]=1)([O-:33])=[O:32]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 1100644-(1,2,4-Triazol-1-yl)phenolHCID 8176205-Bromo-2-nitropyridine

Product 1

HCID 67047909HCID 67047909, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

Cesium carbonate (1.3 g, 4.03 mmol) was mixed with 3 ml of dry dimethylformamide, 4-(1H-1,2,4-triazol-1-yl)phenol (0.5 g, 3.1 mmol) and 5-bromo-2-nitropyridine (0.63 g, 3.1 mmol) and the reaction mixture was heated at stirring at 70° C. in a closed vial. The reaction mixture was then mixed with 40 ml of water and extracted into methylene chloride (3×20 ml). Organic extract was washed with water and brine, dried over magnesium sulfate and concentrated by rotary evaporation. The resulting greenish-brown solid was washed thoroughfully with methylene chloride to give 280 mg of desired compound (32% yield).

Workup

  1. temperaturethe reaction mixture was heated
  2. extractionextracted into methylene chloride (3×20 ml)
  3. extractionOrganic extract
  4. washwas washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated by rotary evaporation
  7. washThe resulting greenish-brown solid was washed thoroughfully with methylene chloride

Sources & evidence

ORD record
ord-1b782506c35541939532aea56a6c7d8e
Source dataset
uspto-grants-2011_03
Patent number
US07915295B2

Reaction notes

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