Water → Ethanol, 2-(ethylphenylamino)-, 1-acetate

HRID 2086530Notes

Reaction equation

HRID 2086530 reaction equation
[CH2:1]([N:3]([CH2:10][CH2:11][OH:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2].C(N(CC)CC)C.[C:20](Cl)(=[O:22])[CH3:21].O>CC(C)=O>[C:20]([O:12][CH2:11][CH2:10][N:3]([CH2:1][CH3:2])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)(=[O:22])[CH3:21]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 623382-(N-ethylanilino)ethanol

Product 1

HCID 113382Ethanol, 2-(ethylphenylamino)-, 1-acetateYield 99.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

51.8 g of 2-(N-ethylanilino)ethanol and 31.7 g of triethylamine were dissolved in 320 ml of acetone, and to this solution 24.9 g of acetyl chloride was slowly added dropwise while stirring under ice cooling. This mixture was stirred for 3 hours at room temperature, and the reaction solution was poured into 500 ml of water. An organic layer was extracted with ethyl acetate, washed with water, and then dried over sodium sulfate. The solvent was distilled off under reduced pressure to obtain 64.9 g of 2-(ethylphenylamino)ethyl acetate.

Workup

  1. stirringThis mixture was stirred for 3 hours at room temperature
  2. extractionAn organic layer was extracted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-dbad21e3b6204aad8f2e74e813b7da0f
Source dataset
uspto-grants-2004_04
Patent number
US06727037B2

Reaction notes

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