Acetone → HCID 17756183, compound

HRID 491589Notes

Reaction equation

HRID 491589 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:11]([F:14])([F:13])[F:12])=[C:8]([OH:10])[CH:9]=1)([O-:3])=[O:2].Cl.[CH3:16][N:17]([CH3:21])[CH2:18][CH2:19]Cl.C([O-])([O-])=O.[K+].[K+].CC(C)=O>O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:11]([F:12])([F:13])[F:14])=[C:8]([O:10][CH2:19][CH2:18][N:17]([CH3:21])[CH3:16])[CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 219595865-Nitro-2-(trifluoromethyl)phenol

Product 1

HCID 17756183HCID 17756183, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-Nitro-2-trifluoromethylphenol (3.48 g, 16.8 mmol) was heated in a sealed tube at 105° C. along with 2-(dimethylamino)ethylchloride hydrochloride (5.32 g, 37.0 mmol), K2CO3 (9.76 g, 70.7 mmol), 114 mL acetone, 33 mL H2O, and Bu4N+I− (0.5 g, 1.34 mmol) for 24 h, then at 120° C. for 24 h. The reaction was cooled to RT and concentrated to aqueous layer, which was diluted with brine and 6 N NaOH and extracted with EtOAc. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. Purification by silica gel column chromatography yielded the title compound as a light brown oil.

Workup

  1. concentrationconcentrated to aqueous layer, which
  2. additionwas diluted with brine and 6 N NaOH
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by silica gel column chromatography

Sources & evidence

ORD record
ord-14b72e18f985445e87646ebb13563990
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

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