Water → HCID 68469062, compound

HRID 503018Notes

Reaction equation

HRID 503018 reaction equation
FC(F)(F)C(O)=O.O.[Cl:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[N:20]([CH3:21])[C:19]([C:22]([CH3:35])([CH3:34])[CH:23]([O:30]COC)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[N:18][N:17]=1>C(Cl)Cl>[Cl:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[N:20]([CH3:21])[C:19]([C:22]([CH3:34])([CH3:35])[CH:23]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[OH:30])=[N:18][N:17]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 68469380HCID 68469380, compound

Product 1

HCID 68469062HCID 68469062, compoundYield 71.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (3 ml) and water (1 ml) were added to a methylene chloride (3 ml) solution of 3-(2-chlorophenyl)-5-[2-(methoxymethoxy)-1,1-dimethyl-2-phenylethyl]-4-methyl-4H-1,2,4-triazole (173 mg) under ice cooling, followed by stirring at room temperature for 19 hours. Then, the whole was stirred at 40° C. for 3.5 hours, at 50° C. for 2.5 hours and at 60° C. for 65 hours. The reaction mixture was concentrated under reduced pressure and ethyl acetate and a saturated sodium hydrogen carbonate solution were added thereto. The organic layer was dried over anhydrous sodium sulfate and then the solvent was removed by evaporation under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=40:1) to obtain 2-[5-(2-chlorophenyl)-4-methyl-4H-1,2,4-triazol-3-yl]-2-methyl-1-phenylpropan-1-ol (110 mg).

Workup

  1. stirringThen, the whole was stirred at 40° C. for 3.5 hours, at 50° C. for 2.5 hours and at 60° C. for 65 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure and ethyl acetate
  3. additiona saturated sodium hydrogen carbonate solution were added
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was removed by evaporation under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (chloroform:methanol=40:1)

Sources & evidence

ORD record
ord-88b9e96f921e4f64b3175855fb46040d
Source dataset
uspto-grants-2010_08
Patent number
US07776897B2

Reaction notes

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