Dimethylamine → HCID 18542959, compound

HRID 649845Notes

Reaction equation

HRID 649845 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5](OS(C(F)(F)F)(=O)=O)=[C:4]([N+:18]([O-:20])=[O:19])[CH:3]=1.[CH3:21][NH:22][CH3:23]>O1CCCC1>[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([N:22]([CH3:23])[CH3:21])=[C:4]([N+:18]([O-:20])=[O:19])[CH:3]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 53760109HCID 53760109, compound

Product 1

HCID 18542959HCID 18542959, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of trifluoro-methanesulfonic acid 4-chloro-5-methoxy-2-nitro-phenyl ester (1.0 g) in tetrahydrofuran (2.0 mL) is added dimethylamine (4.0 mL of a 40% aqueous solution) and the mixture is stirred at room temperature for approximately 15 hours. The solution is then concentrated under reduced pressure and the residue is dissolved in ethyl acetate and then washed with water. The aqueous layer is extracted once with ethyl acetate and the combined organic layers are washed with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate. The solvent is removed by evaporation under reduced pressure and the residue is triturated with hexanes to provide the desired product as a colorless solid.

Workup

  1. concentrationThe solution is then concentrated under reduced pressure
  2. dissolutionthe residue is dissolved in ethyl acetate
  3. washwashed with water
  4. extractionThe aqueous layer is extracted once with ethyl acetate
  5. washthe combined organic layers are washed with saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent is removed by evaporation under reduced pressure
  8. customthe residue is triturated with hexanes

Sources & evidence

ORD record
ord-c7e67d2819454b7498ae1b60f898791c
Source dataset
uspto-grants-2001_08
Patent number
US06271236B1

Reaction notes

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