Ethanolamine → HCID 12017515, compound

HRID 1085286Notes

Reaction equation

HRID 1085286 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]([OH:14])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].S(Cl)(Cl)=O.[CH2:19]([CH2:21][NH2:22])[OH:20].C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl.O.CN(C)C=O>[OH:20][CH2:19][CH2:21][NH:22][C:12](=[O:14])[CH2:11][CH2:10][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=1

Participants

8

Reactant 4

HCID 700EthanolamineHCID 11430Potassium CarbonateHCID 24386Thionyl ChlorideHCID 855263-(4-Nitrophenyl)propanoic acid

Product 1

HCID 12017515HCID 12017515, compoundYield 76.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

60 g of 3-(4-nitrophenyl)propionic acid were suspended in 360 ml of chloroform, followed by the addition of 2.25 g of dimethylformamide. The thus-prepared reaction mixture was heated at 50°-60° C., to which 33.5 ml of thionyl chloride were gradually added dropwise. After the dropwise addition, the resultant mixture was heated under reflux for 1 hour, the solvent was distilled off under reduced pressure, and the resultant oily substance was dissolved in 150 ml of chloroform. The chloroform solution was added dropwise under ice cooling into a solution which had been formed by dissolving 28.2 g of ethanolamine and 42.5 g of potassium carbonate in 450 ml of water. After completion of the dropwise addition, the resultant mixture was stirred for 1 hour. Precipitated crystals were collected by filtration and then recrystallized from 1 of ethyl acetate, thereby obtaining 56.1 g of N-(2-hydroxyethyl)-3-(4-nitrophenyl)propionamide as crystals.

Workup

  1. customThe thus-prepared reaction mixture
  2. additionwere gradually added dropwise
  3. additionAfter the dropwise addition
  4. temperatureunder reflux for 1 hour
  5. distillationthe solvent was distilled off under reduced pressure
  6. dissolutionthe resultant oily substance was dissolved in 150 ml of chloroform
  7. additionThe chloroform solution was added dropwise under ice cooling into a solution which
  8. customhad been formed
  9. additionAfter completion of the dropwise addition
  10. customPrecipitated crystals
  11. filtrationwere collected by filtration
  12. customrecrystallized from 1 of ethyl acetate

Sources & evidence

ORD record
ord-38b79192430746e3b0560ce92db51c13
Source dataset
uspto-grants-1991_04
Patent number
US05008267

Reaction notes

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