Ethanolamine → HCID 69004593, compound

HRID 1436089Notes

Reaction equation

HRID 1436089 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[C:8]([F:10])[C:7]([F:11])=[C:6]([F:12])[CH:5]=1)=O.[CH2:13]([CH2:15][NH2:16])[OH:14]>C1(C)C=CC=CC=1>[F:12][C:6]1[CH:5]=[C:4]([CH:2]([NH:16][CH2:15][CH2:13][OH:14])[CH3:1])[CH:9]=[C:8]([F:10])[C:7]=1[F:11]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 27769073',4',5'-Trifluoroacetophenone

Product 1

HCID 69004593HCID 69004593, compoundYield 34.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3,4,5-trifluoroacetophenone (2.0 g), ethanolamine (2.0 g), and toluene (20 mL) was heated under reflux in a Dean-Stark apparatus for 2.5 hours. The reaction solution was concentrated under reduced pressure, and then the residue was diluted with ethanol (30 mL) and sodium borohydride (1.0 g) was added under ice-cooling. The mixture was stirred at room temperature for three hours and then diluted with a 2 N sodium hydroxide solution and chloroform. Thereafter, the organic layer was separated. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by column chromatography using a silica gel (chloroform:methanol=50:1 to 5:1) to obtain 860 mg of the title compound.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux in a Dean-Stark apparatus for 2.5 hours
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. additionthe residue was diluted with ethanol (30 mL) and sodium borohydride (1.0 g)
  5. additionwas added under ice-
  6. temperaturecooling
  7. additiondiluted with a 2 N sodium hydroxide solution and chloroform
  8. customThereafter, the organic layer was separated
  9. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-89e3608ba1bf452e80ae1995ea951a1b
Source dataset
uspto-grants-2009_11
Patent number
US07618960B2

Reaction notes

Loading…