Water → HCID 23071200, compound

HRID 1625604Notes

Reaction equation

HRID 1625604 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][OH:5].N1C=CC=CC=1.[C:12](Cl)(=[O:16])[O:13][CH2:14][CH3:15].O.[C:19]([O:22][CH2:23][CH3:24])(=[O:21])C>>[C:19](=[O:21])([O:22][CH2:23][CH3:24])[O:5][CH2:4][CH2:3][N:2]([C:12]([O:13][CH2:14][CH3:15])=[O:16])[CH3:1]

Participants

6

Reactant 5

HCID 962WaterHCID 1049PyridineHCID 80162-(Methylamino)ethanolHCID 8857Ethyl AcetateHCID 10928Ethyl chloroformate

Product 1

HCID 23071200HCID 23071200, compound

Procedure

To a solution (1000 mL) of 2-(methylamino)ethanol (100 g) in ethyl acetate was added pyridine (222 mL), ethyl chlorocarbonate (240 mL) was dropwise added over 2 hr. under ice-cooling. After the completion of the dropwise addition, the reaction mixture was stirred at room temperature for 18 hrs. Water (300 mL) was added, and the ethyl acetate layer was separated and washed with 1N hydrochloric acid (200 mL) and saturated brine (200 mL). After drying over anhydrous sodium sulfate, the mixture was concentrated under reduced pressure, and the residue was evaporated under reduced pressure to give the title compound (180 g) as a colorless fraction having a boiling point of 95-100° C. (pressure: 0.1-0.2 mmHg).

Workup

  1. additionwas dropwise added over 2 hr
  2. temperatureunder ice-cooling
  3. additionAfter the completion of the dropwise addition
  4. customthe ethyl acetate layer was separated
  5. washwashed with 1N hydrochloric acid (200 mL) and saturated brine (200 mL)
  6. dry with materialAfter drying over anhydrous sodium sulfate
  7. concentrationthe mixture was concentrated under reduced pressure
  8. customthe residue was evaporated under reduced pressure

Sources & evidence

ORD record
ord-1a4b4e65fb894124971358aaf5db54d9
Source dataset
uspto-grants-2014_07
Patent number
US08784885B2

Reaction notes

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