Water → 2,2,2-Trichloroethyl (1,3-dimethyl-1H-pyrazol-5-yl)carbamate

HRID 2263164Notes

Reaction equation

HRID 2263164 reaction equation
[CH3:1][N:2]1[C:6]([NH2:7])=[CH:5][C:4]([CH3:8])=[N:3]1.Cl[C:10]([O:12][CH2:13][C:14]([Cl:17])([Cl:16])[Cl:15])=[O:11].O>CC(N(C)C)=O>[CH3:1][N:2]1[C:6]([NH:7][C:10](=[O:11])[O:12][CH2:13][C:14]([Cl:17])([Cl:16])[Cl:15])=[CH:5][C:4]([CH3:8])=[N:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 870632,2,2-Trichloroethyl chloroformateHCID 5207211,3-Dimethyl-1H-pyrazol-5-amine

Product 1

HCID 866255062,2,2-Trichloroethyl (1,3-dimethyl-1H-pyrazol-5-yl)carbamateYield 40.8%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1,3-dimethyl-1H-pyrazol-5-amine (500 mg, 4.50 mmol) in dimethylacetamide (15 ml) was added 2,2,2-trichloroethyl chloroformate (0.747 ml, 5.40 mmol) with ice-cooling, and the mixture was stirred at 0° C. for 1 hour. Water was poured into the reaction solution, and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) to give 526 mg (40.8%) of the desired product as an oil.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-dccbff1734a342499fc3f758ec525e42
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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