Potassium Hydroxide → 2,2,2-trichloroethyl 4-bromo-1-methyl-1H-pyrazol-3-ylcarbamate

HRID 1744111Notes

Reaction equation

HRID 1744111 reaction equation
[Br:1][C:2]1[C:3]([N:8](C(OCC(Cl)(Cl)Cl)=O)[C:9]([O:11][CH2:12][C:13]([Cl:16])([Cl:15])[Cl:14])=[O:10])=[N:4][N:5]([CH3:7])[CH:6]=1.[OH-].[K+]>C1COCC1>[Br:1][C:2]1[C:3]([NH:8][C:9](=[O:10])[O:11][CH2:12][C:13]([Cl:14])([Cl:16])[Cl:15])=[N:4][N:5]([CH3:7])[CH:6]=1

Participants

4

Reactant 2

HCID 14797Potassium Hydroxide2×HCID 86594567bis(2,2,2-trichloroethyl) 4-bromo-1-methyl-1H-pyrazol-3-ylimidodicarbonate

Product 1

HCID 691521582,2,2-trichloroethyl 4-bromo-1-methyl-1H-pyrazol-3-ylcarbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To bis(2,2,2-trichloroethyl) 4-bromo-1-methyl-1H-pyrazol-3-ylimidodicarbonate (5.73 g, 10.87 mmol) in THF (50 mL) was added dropwise an aqueous potassium hydroxide solution (2.0 M, 5.7 mL, 11.4 mmol) and the reaction was stirred at rt for 30 minutes. An additional aliquot of aqueous potassium hydroxide (2.0 M, 1.4 mL, 2.8 mmol) was added and the reaction stirred for ½ hour. The reaction was quenched with aqueous saturated ammonium chloride, water was added, the product extracted with Et2O (2×), dried over Na2SO4, concentrated in vacuo and purified by flash chromatography over silica gel (EtOAc/Hex, 1/1) to afford 2,2,2-trichloroethyl 4-bromo-1-methyl-1H-pyrazol-3-ylcarbamate.

Workup

  1. stirringthe reaction stirred for ½ hour
  2. customThe reaction was quenched with aqueous saturated ammonium chloride, water
  3. additionwas added
  4. extractionthe product extracted with Et2O (2×)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. custompurified by flash chromatography over silica gel (EtOAc/Hex, 1/1)

Sources & evidence

ORD record
ord-c361c0fff9484566a54d8556a8712d89
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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