Phenyl chloroformate → phenyl (3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)carbamate

HRID 1182111Notes

Reaction equation

HRID 1182111 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]([NH2:10])[N:7]([CH3:9])[N:8]=2)[CH2:3][CH2:2]1.C(=O)(O)[O-].[Na+].[C:16]1([O:22][C:23](Cl)=[O:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1COCC1>[C:16]1([O:22][C:23](=[O:24])[NH:10][C:6]2[N:7]([CH3:9])[N:8]=[C:4]([CH:1]3[CH2:3][CH2:2]3)[CH:5]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 15891Phenyl chloroformateHCID 516892Sodium BicarbonateHCID 27353113-cyclopropyl-1-methyl-1H-pyrazol-5-amine

Product 1

HCID 69361078phenyl (3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-Cyclopropyl-2-methyl-2H-pyrazol-3-ylamine (3.0 g, 22 mmol) (65 ml) and sodium bicarbonate (2 g, 24 mmol) in THF is cooled to 0° C. Phenylchloroformate (3.4 g, 22 mmol) is added dropwise over 15 minutes. The reaction mixture is allowed to warm to ambient temperature and stirred for 5 hours, then filtered and the filtrate partitioned between ethylacetate and water. The organic phase is washed with water, 5% aqueous citric acid solution and brine, dried over MgSO4 and evaporated to afford (5-Cyclopropyl-2-methyl-2H-pyrazol-3-yl)-carbamic acid phenyl ester. [M+H] 258.17.

Workup

  1. filtrationfiltered
  2. customthe filtrate partitioned between ethylacetate and water
  3. washThe organic phase is washed with water, 5% aqueous citric acid solution and brine
  4. dry with materialdried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-5fd4f68095694edaa9ef65ff84060ba1
Source dataset
uspto-grants-2007_10
Patent number
US07288537B2

Reaction notes

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