Water → HCID 23071200, compound

HRID 2096050Notes

Reaction equation

HRID 2096050 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 of 2-(methylamino)ethanol (100 g) in ethyl acetate (1000 mL) was added pyridine (222 mL), and added dropwise ethyl chlorocarbonate (240 mL) over 2 hrs under ice-cooling. After the addition, the reaction solution was stirred at room temperature for 18 hrs. To the solution was added water (300 mL), and the ethyl acetate layer was separated. The ethyl acetate layer was washed with 1 N hydrochloric acid (200 mL) and saturated brine (200 mL), and dried over anhydrous sodium sulfate, followed by concentrating under reduce pressure. The residue was distilled under reduce pressure to give title compound (180 g) as colorless fraction having boiling point of 95-100° C. (pressure: 0.1-0.2 mmHg).

Workup

  1. temperaturecooling
  2. additionAfter the addition
  3. customthe ethyl acetate layer was separated
  4. washThe ethyl acetate layer was washed with 1 N hydrochloric acid (200 mL) and saturated brine (200 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationby concentrating
  7. distillationThe residue was distilled

Sources & evidence

ORD record
ord-7602fc7a2b444b5e8ce386080649bb89
Source dataset
uspto-grants-2013_05
Patent number
US08449911B2

Reaction notes

Loading…