1,4-Dioxane → 4-[1-(4-pentafluoroethyloxyphenyl)-1H-[1,2,4]triazol-3-yl]-phenylamine

HRID 2207012Notes

Reaction equation

HRID 2207012 reaction equation
[F:1][C:2]([F:33])([O:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH:18]=[N:17][C:16]([C:19]3[CH:24]=[CH:23][C:22]([NH:25]C(=O)OC(C)(C)C)=[CH:21][CH:20]=3)=[N:15]2)=[CH:10][CH:9]=1)[C:3]([F:6])([F:5])[F:4].O1CCOCC1.C([O-])(O)=O.[Na+]>Cl>[F:33][C:2]([F:1])([O:7][C:8]1[CH:9]=[CH:10][C:11]([N:14]2[CH:18]=[N:17][C:16]([C:19]3[CH:20]=[CH:21][C:22]([NH2:25])=[CH:23][CH:24]=3)=[N:15]2)=[CH:12][CH:13]=1)[C:3]([F:6])([F:5])[F:4]

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 516892Sodium BicarbonateHCID 86668344{4-[1-(4-pentafluoroethyloxyphenyl)-1H-[1,2,4]triazol-3-yl]-phenyl}-carbamic acid tert-butyl ester

Product 1

HCID 782102294-[1-(4-pentafluoroethyloxyphenyl)-1H-[1,2,4]triazol-3-yl]-phenylamineYield 68%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
40 °C

Procedure

Tert-butyl (4-(1-(4-(perfluoroethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)carbamate (0.100 g, 0.213 mol) was dissolved in HCl in dioxane (4 N, 3 mL, 12 mmol) and stirred at 40° C. for 1 h. The solutionwas then cooled, neutralized with saturated aqueous NaHCO3 solution to pH 7, and extracted with diethyl ether (2×10 mL). The combined organic layer was dried and concentrated to afford the title compound as a light tan solid (54 mg, 68%): 1H NMR (400 MHz, CDCl3) δ 8.52 (s, 1H), 7.99 (d, J=8.6 Hz, 1H), 7.79 (d, J=9.0 Hz, 1H), 7.37 (d, J=8.8 Hz, 1H), 6.76 (d, J=8.6 Hz, 1H). 3.9 (br s, 2H); ESIMS m/z 371 ([M+H]+).

Workup

  1. temperatureThe solutionwas then cooled
  2. extractionextracted with diethyl ether (2×10 mL)
  3. customThe combined organic layer was dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ec82cc2963fc4281b76c1505ab3cdc34
Source dataset
uspto-grants-2016_06
Patent number
US09376401B2

Reaction notes

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