Water → 4-trifluoromethylphenyl N-(6-methoxy-2-pyridyl)-N-methylcarbamate

HRID 1583703Notes

Reaction equation

HRID 1583703 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([NH:9][CH3:10])[N:4]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:18]([O:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=1)=[O:19].O>CC(C)=O>[CH3:1][O:2][C:3]1[N:4]=[C:5]([N:9]([CH3:10])[C:18](=[O:19])[O:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=2)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 70191686-methoxy-N-methylpyridin-2-amineHCID 159175974-(Trifluoromethyl)phenyl carbonochloridate

Product 1

HCID 133875774-trifluoromethylphenyl N-(6-methoxy-2-pyridyl)-N-methylcarbamateYield 62%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To the mixture of 1.38 g of 2-methoxy-6-methylaminopyridine and 1.38 g of anhydrous potassium carbonate in 20 ml of acetone was added dropwise the solution of 2.25 g of 4-trifluoromethylphenyl chloroformate in 20 ml of acetone under stirring at room temperature. The mixture was stirred for 30 minutes and then was refluxed for 2 hours. After the reaction mixture was cooled to room temperature, it was poured into water and the product was extracted with benzene. The benzene solution, successively washed with water and brine, was dried over anhydrous magnesium sulfate. The residue obtained by the removal of benzene under reduced pressure was chromatographed through silica gel column using benzene as an eluent to give 2.02 g of pure 4-trifluoromethylphenyl N-(6-methoxy-2-pyridyl)-N-methylcarbamate as solid in the yield of 62%. A part of the solid was recrystallized from hexane and crystalls having melting point of 85° to 86° C. were obtained.

Workup

  1. stirringThe mixture was stirred for 30 minutes
  2. temperaturewas refluxed for 2 hours
  3. temperatureAfter the reaction mixture was cooled to room temperature
  4. extractionthe product was extracted with benzene
  5. washThe benzene solution, successively washed with water and brine
  6. dry with materialwas dried over anhydrous magnesium sulfate
  7. customThe residue obtained by the removal of benzene under reduced pressure
  8. customwas chromatographed through silica gel column

Sources & evidence

ORD record
ord-baa0b19a408d4b28a849a04cd0e9275f
Source dataset
uspto-grants-1985_11
Patent number
US04554012

Reaction notes

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