Water → HCID 136352700, compound

HRID 389130Notes

Reaction equation

HRID 389130 reaction equation
C[S-].[Na+].[ClH:4].C[O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:17]([CH3:18])[C:16]([C:19]([CH3:32])([O:21][C:22]3[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=3)[CH3:20])=[N:15][N:14]=2)=[C:9]([C:33]([F:36])([F:35])[F:34])[CH:8]=1.O>CN(C=O)C>[ClH:4].[CH3:18][N:17]1[C:16]([C:19]([CH3:32])([O:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:30])([F:31])[F:29])=[CH:24][CH:23]=2)[CH3:20])=[N:15][N:14]=[C:13]1[C:10]1[CH:11]=[CH:12][C:7]([OH:6])=[CH:8][C:9]=1[C:33]([F:34])([F:36])[F:35]

Participants

5

Reactant 3

HCID 962WaterHCID 4378561Sodium methanethiolateHCID 86653017HCID 86653017, compound

Product 1

HCID 136352700HCID 136352700, compoundYield 42.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Sodium thiomethoxide (30 mg) was added to a solution of 3-[4-methoxy-2-(trifluoromethyl)phenyl]-4-methyl-5-{1-methyl-1-[4-(trifluoromethyl)phenoxy]ethyl}-4H-1,2,4-triazole monohydrochloride (87 mg) in DMF (3 ml) under a nitrogen atmosphere, followed by stirring at 100° C. for 17 hours. The reaction solution was stood to cool to room temperature, and water was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with water and then saturated brine in this order and dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by thin layer chromatography (ethyl acetate). The resulting residue was powdered with diisopropylether, the resulting solid was dissolved in ethyl acetate (1 ml), and 4M hydrogen chloride-ethyl acetate was added thereto. The precipitated solid was collected by filtration and dried under reduced pressure to obtain, as a colorless solid, 4-(4-methyl-5-{1-methyl-1-[4-(trifluoromethyl)phenoxy]ethyl}-4H-1,2,4-triazol-3-yl)-3-(trifluoromethyl)phenol monohydrochloride (36 mg).

Workup

  1. temperatureto cool to room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialsaturated brine in this order and dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by thin layer chromatography (ethyl acetate)
  7. dissolutionthe resulting solid was dissolved in ethyl acetate (1 ml)
  8. addition4M hydrogen chloride-ethyl acetate was added
  9. filtrationThe precipitated solid was collected by filtration
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-2e586b74e9404379987732818da20de7
Source dataset
uspto-grants-2013_02
Patent number
US08377923B2

Reaction notes

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