Sodium Hydroxide → 2,2,2-Trichloroethyl 3-tert-butyl-1-P-tolyl-1H-pyrazol-5-ylcarbamate

HRID 909223Notes

Reaction equation

HRID 909223 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH2:17])[N:8]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)[N:9]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].[Cl:20][C:21]([Cl:28])([Cl:27])[CH2:22][O:23][C:24](Cl)=[O:25]>O.C(OCC)(=O)C>[Cl:20][C:21]([Cl:28])([Cl:27])[CH2:22][O:23][C:24](=[O:25])[NH:17][C:7]1[N:8]([C:10]2[CH:11]=[CH:12][C:13]([CH3:16])=[CH:14][CH:15]=2)[N:9]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:6]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 870632,2,2-Trichloroethyl chloroformateHCID 29741323-tert-butyl-1-(4-methylphenyl)-1H-pyrazol-5-amine

Product 1

HCID 99310942,2,2-Trichloroethyl 3-tert-butyl-1-P-tolyl-1H-pyrazol-5-ylcarbamateYield 99.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A cooled (0° C.) biphasic solution of 5-tert-butyl-2-p-tolyl-2H-pyrazol-3-ylamine (26.6 g, 100 mmol) in water (80 mL) and ethyl acetate (180 mL) was treated with NaOH (10 g, 250 mmol) followed by trichloroethylchloroformate (29.7 g, 140 mmol). The reaction mixture was warmed to room temperature and stirred for 1 hour. The layers were separated and the organic layer was washed with brine (100 mL), dried over MgSO4, filtered through Celite, and concentrated under reduced pressure to provide 40.3 g of pale yellow solid (99% yield).

Workup

  1. customThe layers were separated
  2. washthe organic layer was washed with brine (100 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered through Celite
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1f8c406c774049ad86cfe749523ae401
Source dataset
uspto-grants-2011_09
Patent number
US08017641B2

Reaction notes

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