Potassium Carbonate → phenyl 1-tert-butyl-1H-pyrazol-4-ylcarbamate

HRID 1918020Notes

Reaction equation

HRID 1918020 reaction equation
[C:1]([N:5]1[CH:9]=[C:8]([NH2:10])[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[C:11]1([O:17][C:18](Cl)=[O:19])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C([O-])([O-])=O.[K+].[K+]>C1COCC1>[C:1]([N:5]1[CH:9]=[C:8]([NH:10][C:18](=[O:19])[O:17][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15891Phenyl chloroformateHCID 134698171-(tert-butyl)-1H-pyrazol-4-amine

Product 1

HCID 66876267phenyl 1-tert-butyl-1H-pyrazol-4-ylcarbamateYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution containing 1-tert-butyl-1H-pyrazol-4-amine (0.995 g, 7.16 mmol) in THF (20 mL), phenylchloroformate (1.00 mL, 8.02 mmol) and K2CO3 (1.32 g, 9.52 mmol) were added at room temperature. After stirring overnight, the mixture was filtered and the solid washed with THF. The filtrate was concentrated to dryness and the residue was dissolved in DCM and the organic solution was washed with brine and dried over MgSO4 to yield phenyl 1-tert-butyl-1H-pyrazol-4-ylcarbamate as a solid (1.65 g, 89%). 1H NMR (300 MHz, CDCl3) δ 7.85 (1H, s), 7.30 (6H, m), 1.60 (9H, s).

Workup

  1. additionwere added at room temperature
  2. filtrationthe mixture was filtered
  3. washthe solid washed with THF
  4. concentrationThe filtrate was concentrated to dryness
  5. dissolutionthe residue was dissolved in DCM
  6. washthe organic solution was washed with brine
  7. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-ecb9e2eb5822467fb4bb9b81c64e906d
Source dataset
uspto-grants-2013_12
Patent number
US08618289B2

Reaction notes

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