p-Toluenesulfonic acid → 3-(2-phenoxyethoxy)-1H-pyrazol-5-amine

HRID 2054372Notes

Reaction equation

HRID 2054372 reaction equation
[O:1]([CH2:8][CH2:9][OH:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:11][C:12]1[CH:16]=[C:15](O)[NH:14][N:13]=1.CC1C=CC(S(O)(=O)=O)=CC=1>>[O:1]([CH2:8][CH2:9][O:10][C:15]1[CH:16]=[C:12]([NH2:11])[NH:13][N:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 31236PhenoxyethanolHCID 962215-Amino-1H-pyrazol-3-ol

Product 1

HCID 189815973-(2-phenoxyethoxy)-1H-pyrazol-5-amineYield 30.7%

Conditions

Temperature
130 °C

Procedure

A mixture of 2-phenoxyethanol (56.1 g, 406 mmol), 3-amino-1H-pyrazol-5-ol (8.0648 g, 81.4 mmol) and TsOH (30.96 g, 162.8 mmol) was stirred at 130° C. under vacuum for 11 h. After cooled down to room temperature, the solid was washed with MeCN (200 mL), then treated with 6% aqueous NaHCO3 solution (500 mL). The suspension was filtered, and the solid collected was dissolved in EtOAc (100 mL), dried over MgSO4, filtered and concentrated, giving the title compound (5.4734 g, 30.7% yield). ESI m/z=220.19 [(M+1)+; calcd for C11H13N3O2+H: 220.11].

Workup

  1. temperatureAfter cooled down to room temperature
  2. washthe solid was washed with MeCN (200 mL)
  3. additiontreated with 6% aqueous NaHCO3 solution (500 mL)
  4. filtrationThe suspension was filtered
  5. customthe solid collected
  6. dissolutionwas dissolved in EtOAc (100 mL)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-35289dbeca314818adb16b4c148cb178
Source dataset
uspto-grants-2008_02
Patent number
US07329668B2

Reaction notes

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