Water → HCID 58243914, compound

HRID 389116Notes

Reaction equation

HRID 389116 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:13]([F:16])([F:15])[F:14])=[N:5][N:4]=[C:3]1[CH:17]([O:19][C:20]1[N:27]=[CH:26][CH:25]=[CH:24][C:21]=1[C:22]#[N:23])[CH3:18].[OH-:28].[Na+].O>C(O)C>[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:13]([F:16])([F:15])[F:14])=[N:5][N:4]=[C:3]1[CH:17]([O:19][C:20]1[N:27]=[CH:26][CH:25]=[CH:24][C:21]=1[C:22]([NH2:23])=[O:28])[CH3:18]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 58243511HCID 58243511, compound

Product 1

HCID 58243914HCID 58243914, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

2-(1-{4-methyl-5-[2-(trifluoromethyl)phenyl]-4H-1,2,4-triazol-3-yl}ethoxy)nicotinonitrile (270 mg) was dissolved in ethanol (10 ml), a 1M aqueous sodium hydroxide solution (3.7 ml) was added thereto, followed by stirring at 70° C. for 5 hours. The reaction solution was cooled to room temperature, and water was added thereto, followed by extraction with chloroform. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting solid was washed with ethyl acetate, to obtain, as a colorless solid, 2-(1-{4-methyl-5-[2-(trifluoromethyl)phenyl]-4H-1,2,4-triazol-3-yl}ethoxy)nicotinamide (120 mg).

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. extractionfollowed by extraction with chloroform
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washThe resulting solid was washed with ethyl acetate

Sources & evidence

ORD record
ord-296d2df416c04870a0093b9eed055aa2
Source dataset
uspto-grants-2013_02
Patent number
US08377923B2

Reaction notes

Loading…