Water → HCID 86245085, compound

HRID 2263135Notes

Reaction equation

HRID 2263135 reaction equation
[CH3:1][N:2]1[C:6]([NH2:7])=[CH:5][CH:4]=[N:3]1.N1C=CC=CC=1.Cl[C:15]([O:17][CH2:18][C:19]([Cl:22])([Cl:21])[Cl:20])=[O:16].O>O1CCCC1>[CH3:1][N:2]1[C:6]([NH:7][C:15](=[O:16])[O:17][CH2:18][C:19]([Cl:22])([Cl:21])[Cl:20])=[CH:5][CH:4]=[N:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 870632,2,2-Trichloroethyl chloroformateHCID 1369272-Methyl-2H-pyrazol-3-ylamine

Product 1

HCID 86245085HCID 86245085, compoundYield 50.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-methyl-1H-pyrazole-5-amine (1.00 g, 10.3 mmol) and pyridine (1.01 ml, 12.4 mmol) in tetrahydrofuran (34 ml) was added 2,2,2-trichloroethyl chloroformate (1.71 ml, 12.4 mmol) with ice-cooling and the mixture was stirred at room temperature for 1 hour. Water was added to the reaction mixture 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 (hexane:ethyl acetate=1:1) to obtain the desired product (1.43 g, 50.8%) 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 (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-de621059310f4c4296f4c869080c49f8
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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