Water → HCID 86653018, compound

HRID 389133Notes

Reaction equation

HRID 389133 reaction equation
[ClH:1].[CH3:2][N:3]1[C:7]([C:8]([CH3:20])([O:10][C:11]2[C:16]([F:17])=[CH:15][C:14]([F:18])=[CH:13][C:12]=2[F:19])[CH3:9])=[N:6][N:5]=[C:4]1[C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][C:22]=1[C:28]([F:31])([F:30])[F:29].C(=O)([O-])[O-].[K+].[K+].Br[CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41].O>CN(C=O)C>[ClH:1].[CH3:2][N:3]1[C:7]([C:8]([CH3:20])([O:10][C:11]2[C:12]([F:19])=[CH:13][C:14]([F:18])=[CH:15][C:16]=2[F:17])[CH3:9])=[N:6][N:5]=[C:4]1[C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41])=[CH:23][C:22]=1[C:28]([F:31])([F:30])[F:29]

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 136352701HCID 136352701, compound

Product 1

HCID 86653018HCID 86653018, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

4-{4-methyl-5-[1-methyl-1-(2,4,6-trifluorophenoxy)ethyl]-4H-1,2,4-triazol-3-yl}-3-(trifluoromethyl)phenol monohydrochloride (123 mg) was suspended in DMF (3 ml), and potassium carbonate (182 mg) and ethyl bromoacetate (0.060 ml) were added thereto, followed by stirring at 60° C. for one hour. The reaction solution was cooled to room temperature and water was added thereto followed by extraction with ethyl acetate. The organic layer was sequentially washed with water and saturated brine in this order and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The resulting residue was dissolved in ethyl acetate, 4M hydrogen chloride-ethyl acetate (1 ml) was added thereto and the solvent was evaporated under reduced pressure. The residue was washed with diisopropylether to obtain, as a white solid, ethyl [4-{4-methyl-5-[1-methyl-1-(2,4,6-trifluorophenoxy)ethyl]-4H-1,2,4-triazol-3-yl}-3-(trifluoromethyl)phenoxy}acetate monohydrochloride (68 mg).

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. extractionthereto followed by extraction with ethyl acetate
  3. washThe organic layer was sequentially washed with water and saturated brine in this order
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. dissolutionThe resulting residue was dissolved in ethyl acetate
  7. addition4M hydrogen chloride-ethyl acetate (1 ml) was added
  8. customthe solvent was evaporated under reduced pressure
  9. washThe residue was washed with diisopropylether

Sources & evidence

ORD record
ord-3d872e136db94faeaae65e562ef1462e
Source dataset
uspto-grants-2013_02
Patent number
US08377923B2

Reaction notes

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