2-(Dimethylamino)ethanol → Carbonic acid, 2-(dimethylamino)ethyl phenyl ester

HRID 1734388Notes

Reaction equation

HRID 1734388 reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][OH:5].C(N(CC)CC)C.[C:14]1([O:20][C:21](Cl)=[O:22])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1(C)C=CC=CC=1>[O:20]([C:21]([O:5][CH2:4][CH2:3][N:2]([CH3:6])[CH3:1])=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 79022-(Dimethylamino)ethanolHCID 8471TriethylamineHCID 15891Phenyl chloroformate

Product 1

HCID 11117296Carbonic acid, 2-(dimethylamino)ethyl phenyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a 500 ml three-necked round-bottomed flask equipped with an internal thermometer, reflux condenser, mechanical stirrer, addition funnel, and argon inlet are added N,N-dimethylethanolamine (25.00 g, 0.281 mol), toluene (200 ml), and triethylamine (31.21 g, 0.309 mol). The mixture is treated with a solution of phenylchloroformate (43.91 g, 0.281 mol) dissolved in 50 ml of toluene over 15 min. After addition is complete, the mixture is heated to reflux for 3 h. The cooled mixture is washed with saturated sodium bicarbonate solution (2×100 ml) and water (100 ml). The organic phase is dried over MgSO4, filtered, and concentrated first by rotary evaporation at 50° C. (water aspirator vacuum) and then at 60° C. (0.05 mmHg) in a Kugelrohr oven to give 8 as a light yellow oil, 49.93 g (85%) that crystallizes on standing.

Workup

  1. customTo a 500 ml three-necked round-bottomed flask equipped with an internal thermometer
  2. temperaturereflux
  3. additioncondenser, mechanical stirrer, addition funnel, and argon inlet
  4. additionAfter addition
  5. temperaturethe mixture is heated
  6. temperatureto reflux for 3 h
  7. washThe cooled mixture is washed with saturated sodium bicarbonate solution (2×100 ml) and water (100 ml)
  8. dry with materialThe organic phase is dried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated first by rotary evaporation at 50° C. (water aspirator vacuum)

Sources & evidence

ORD record
ord-d039efa39fe04407a5041cc82af32a56
Source dataset
uspto-grants-1996_07
Patent number
US05534179

Reaction notes

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