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

HRID 1921287Notes

Reaction equation

HRID 1921287 reaction equation
Cl.[C:2]([C:6]1[CH:10]=[C:9]([NH2:11])[N:8]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[N:7]=1)([CH3:5])([CH3:4])[CH3:3].[OH-].[Na+].[C:21](Cl)(=[O:28])[O:22][CH2:23][C:24]([Cl:27])([Cl:26])[Cl:25]>CCOC(C)=O>[Cl:25][C:24]([Cl:27])([Cl:26])[CH2:23][O:22][C:21](=[O:28])[NH:11][C:9]1[N:8]([C:12]2[CH:13]=[CH:14][C:15]([CH3:18])=[CH:16][CH:17]=2)[N:7]=[C:6]([C:2]([CH3:5])([CH3:4])[CH3:3])[CH:10]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 870632,2,2-Trichloroethyl chloroformateHCID 119912003-(tert-Butyl)-1-(p-tolyl)-1H-pyrazol-5-amine hydrochloride

Product 1

HCID 99310942,2,2-Trichloroethyl 3-tert-butyl-1-P-tolyl-1H-pyrazol-5-ylcarbamateYield 51.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 3-tert-butyl-1-(4-methylphenyl)-1H-pyrazol-5-amine hydrochloride (2.5 g) in EtOAc (18 ml) was added 2.94 M aqueous NaOH (8 mL) at 0° C. under a nitrogen atmosphere, and the mixture was stirred at the same temperature for 15 min. To the reaction mixture was added 2,2,2-trichloroethyl chlorocarbonate (2.79 g), and the resulting mixture was stirred at room temperature for 6 hr. The organic layer was separated and successively washed with brine (10 mL×2), dried over MgSO4, filtered and evaporated in vacuo. The residue was triturated with IPE, and the precipitates produced were collected by filtration to give 2,2,2-trichloroethyl[3-tert-butyl-1-(4-methylphenyl)-1H-pyrazol-5-yl]carbamate (1.96 g).

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 6 hr
  2. customThe organic layer was separated
  3. washsuccessively washed with brine (10 mL×2)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was triturated with IPE
  8. customthe precipitates produced
  9. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-4c92c6f9db5640b7936e09c003b962f5
Source dataset
uspto-grants-2012_05
Patent number
US08173684B2

Reaction notes

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