2-Chloroethanol → N-(2-hydroxyethyl)-3,5-dimethyl-4-fluoroaniline

HRID 2255006Notes

Reaction equation

HRID 2255006 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([CH3:10])[C:8]=1[F:9])[NH2:5].Cl[CH2:12][CH2:13][OH:14]>C(O)C.[OH-].[Na+]>[OH:14][CH2:13][CH2:12][NH:5][C:4]1[CH:6]=[C:7]([CH3:10])[C:8]([F:9])=[C:2]([CH3:1])[CH:3]=1

Participants

5

Reactant 2

HCID 342-ChloroethanolHCID 191033484-Fluoro-3,5-dimethylaniline

Product 1

HCID 19739527N-(2-hydroxyethyl)-3,5-dimethyl-4-fluoroanilineYield 86.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

In a mixed solution of 100 ml of ethanol and 60 ml of a 2N-NaOH solution were dissolved 12.3 g of the 3,5-dimethyl-4-fluoroaniline and 81 g of 2-chloroethanol, and the resulting solution was subjected to reaction with refluxing for 3 hours. After completion of the reaction, the ethanol was distilled off and the residue was extracted with ethyl acetate, after which the extract was washed with water, dried and then concentrated to obtain 14 g of crude N-(2-hydroxyethyl)-3,5-dimethyl-4-fluoroaniline. Subsequently, this crude compound was dissolved in 100 ml of isopropanol, followed by adding thereto 15 g of iodoethane and 20 g of potassium carbonate, and the reaction was carried out with refluxing for 5 hours. After completion of the reaction, the solvent was distilled off and the residue was extracted with ethyl acetate, and the extract was washed with water, dried and then concentrated to obtain 16 g of a crude product of the desired compound. The crude product was purified by a column chromatography (packing; Wakogel C-300, a registered trade name, mfd. by Wako Pure Chemical Industries, Ltd., eluent: ethyl acetate : n-hexane =1 : 2) to obtain 9.5 g of oily N-ethyl-N-(2-hydroxyethyl)-3,5-dimethyl-4-fluoroaniline.

Workup

  1. customthe resulting solution was subjected to reaction
  2. temperaturewith refluxing for 3 hours
  3. customAfter completion of the reaction
  4. distillationthe ethanol was distilled off
  5. extractionthe residue was extracted with ethyl acetate
  6. washafter which the extract was washed with water
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-322f4e090590416a8bf3ea80e76e3391
Source dataset
uspto-grants-1993_08
Patent number
US05238818

Reaction notes

Loading…