N-Methyldiethanolamine → N,N-Bis[2-((phenoxycarbonyl)oxy)ethyl]-N-methylamine

HRID 51987

Reaction equation

HRID 51987 reaction equation
[CH3:1][N:2]([CH2:6][CH2:7][OH:8])[CH2:3][CH2:4][OH:5].C(N([CH2:14][CH3:15])CC)C.[C:16]1([O:22][C:23](Cl)=[O:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1(C)C=CC=CC=1>[O:22]([C:23]([O:5][CH2:4][CH2:3][N:2]([CH2:6][CH2:7][O:8][C:23]([O:24][C:15]1[CH:14]=[CH:18][CH:17]=[CH:16][CH:21]=1)=[O:22])[CH3:1])=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7767N-MethyldiethanolamineHCID 8471TriethylamineHCID 15891Phenyl chloroformate

Product 1

HCID 19962809N,N-Bis[2-((phenoxycarbonyl)oxy)ethyl]-N-methylamine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
45 °C

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-methyldiethanolamine (20.00 g, 0.168 mol), toluene (200 ml), and triethylamine (37.36 g, 0.369 mol). The minute is treated with a solution of phenylchloroformate (52.56 g, 0.336 mol dissolved in 50 ml of toluene so as to maintain the reaction temperature at 35°-45° C. After addition is complete, the mixture is heated at 45° C. for an additional 1.5 h. The cooled mixture is washed with saturated sodium bicarbonate solution (2×200 ml) and water (200 ml). The organic phase is dried over MgSO4, filtered, and concentrated first by rotary evaporation at 50° C. (water aspirator vacuum) and then at 80° C. (0.02 mmHg) in a Kugelrohr oven to give 3 as a light yellow oil, 55.65 g (92%) 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. temperatureto maintain the reaction temperature at 35°-45° C
  5. additionAfter addition
  6. washThe cooled mixture is washed with saturated sodium bicarbonate solution (2×200 ml) and water (200 ml)
  7. dry with materialThe organic phase is dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated first by rotary evaporation at 50° C. (water aspirator vacuum)

Sources & evidence

ORD record
ord-2085c51b61b847ae9cb53b95d77445f8
Source dataset
uspto-grants-1997_04
Patent number
US05616546

Linked notes

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