Sodium Hydroxide → HCID 45926015, compound

HRID 1663668Notes

Reaction equation

HRID 1663668 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([NH2:10])[N:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].[C:19](Cl)(=[O:26])[O:20][CH2:21][C:22]([Cl:25])([Cl:24])[Cl:23]>C(OCC)(=O)C>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:19](=[O:26])[O:20][CH2:21][C:22]([Cl:25])([Cl:24])[Cl:23])[N:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 870632,2,2-Trichloroethyl chloroformateHCID 7706343-tert-butyl-1-phenyl-1H-pyrazol-5-amine

Product 1

HCID 45926015HCID 45926015, compoundYield 55.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a two-phase solution of 3-tert-butyl-1-phenyl-1H-pyrazol-5-amine (5.0 g, 23 mmol) in ethyl acetate (45 mL)/3N aqueous sodium hydroxide (20 mL) was added 2,2,2-trichloroethyl chlorocarbonate (4.5 mL, 33 mmol) under ice-cooling, and the mixture was stirred at room temperature for 2 hr. The obtained organic layer was washed with 5% aqueous sodium hydrogencarbonate, water and saturated brine, dried over anhydrous sodium sulfate, and filtrated. The solvent was evaporated under reduced pressure to give the title compound (5.0 g, 55%) as a white powder.

Workup

  1. temperaturecooling
  2. washThe obtained organic layer was washed with 5% aqueous sodium hydrogencarbonate, water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltrated
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-13263282eafb4492835e794419619525
Source dataset
uspto-grants-2011_10
Patent number
US08034812B2

Reaction notes

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