Dimethyl Sulfate → HCID 23363109, compound

HRID 1081865Notes

Reaction equation

HRID 1081865 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:15]([O-:17])=[O:16])=[C:6]([CH:14]=1)[NH:7][C:8](=[O:13])[C:9]([F:12])([F:11])[F:10].[C:18](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>CC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:15]([O-:17])=[O:16])=[C:6]([CH:14]=1)[N:7]([CH3:18])[C:8](=[O:13])[C:9]([F:10])([F:12])[F:11]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 10730652HCID 10730652, compound

Product 1

HCID 23363109HCID 23363109, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

5-Chloro-2-nitro-N-trifluoroacetylaniline (38 g) from Example 8 was dissolved in acetone (300 ml), followed by addition of potassium carbonate (19.5 g). To the mixture was added dropwise dimethyl sulfate (13.4 ml) for subsequent stirring for 1.5 hours. After filtering off insoluble inorganic materials, the resulting material was washed with ethyl acetate. Removal of the solvent under reduced pressure, hexane was added to the residue under stirring, to separate the crystal by filtration. By washing the crystal further with ether-hexane mixture solution, the title compound was given (33 g; 83.5%).

Workup

  1. filtrationAfter filtering off insoluble inorganic materials
  2. washthe resulting material was washed with ethyl acetate
  3. customRemoval of the solvent under reduced pressure, hexane
  4. additionwas added to the residue
  5. stirringunder stirring
  6. customto separate the crystal
  7. filtrationby filtration
  8. washBy washing the crystal further with ether-hexane mixture solution

Sources & evidence

ORD record
ord-65b965b7d367479e999a76407731a54c
Source dataset
uspto-grants-1996_12
Patent number
US05587392

Reaction notes

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