Methanol → HCID 58244210, compound

HRID 389126Notes

Reaction equation

HRID 389126 reaction equation
[CH3:1][C:2]([C:14]1[N:18]([CH3:19])[C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:26]([F:29])([F:28])[F:27])=[N:16][N:15]=1)([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1)[CH3:3].S(=O)(=O)(O)O.[CH3:35]O>C(OCC)(=O)C>[CH3:3][C:2]([C:14]1[N:18]([CH3:19])[C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:26]([F:28])([F:29])[F:27])=[N:16][N:15]=1)([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([O:11][CH3:35])=[O:10])=[CH:7][CH:6]=1)[CH3:1]

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 58243721HCID 58243721, compound

Product 1

HCID 58244210HCID 58244210, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-(1-methyl-1-{4-methyl-5-[2-(trifluoromethyl)phenyl]-4H-1,2,4-triazol-3-yl}ethoxy)benzoic acid (400 mg) was dissolved in methanol (12 ml), concentrated sulfuric acid (0.160 ml) was added thereto, followed by heating to reflux for 2 days. The reaction solution was cooled to room temperature, diluted with ethyl acetate and was washed with a 1M aqueous sodium hydroxide solution, water and saturated brine in this order. The organic layer was dried over anhydrous magnesium sulfate and then concentrated. The resulting solid was washed with diisopropylether to obtain methyl 4-(1-methyl-1-{4-methyl-5-[2-(trifluoromethyl)phenyl]-4H-1,2,4-triazol-3-yl}ethoxy)benzoate (249 mg), as a white solid.

Workup

  1. temperatureby heating
  2. temperatureto reflux for 2 days
  3. washwas washed with a 1M aqueous sodium hydroxide solution, water and saturated brine in this order
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. washThe resulting solid was washed with diisopropylether

Sources & evidence

ORD record
ord-040785344af14941ae657208a49edbfd
Source dataset
uspto-grants-2013_02
Patent number
US08377923B2

Reaction notes

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