Ethanolamine → 2,2,2-Trichloroethyl (2-hydroxyethyl)carbamate

HRID 1448483Notes

Reaction equation

HRID 1448483 reaction equation
[NH2:1][CH2:2][CH2:3][OH:4].C(=O)([O-])[O-].[Na+].[Na+].[Cl:11][C:12]([Cl:19])([Cl:18])[CH2:13][O:14][C:15](Cl)=[O:16]>CC(C)=O.O>[Cl:11][C:12]([Cl:19])([Cl:18])[CH2:13][O:14][C:15]([NH:1][CH2:2][CH2:3][OH:4])=[O:16]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 10340Sodium CarbonateHCID 870632,2,2-Trichloroethyl chloroformate

Product 1

HCID 203798712,2,2-Trichloroethyl (2-hydroxyethyl)carbamate

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Conditions

Temperature
0 °C

Procedure

2-Aminoethanol (20 g.) and sodium carbonate (27.8 g.) is dissolved in acetone-water (4:1) (500 ml.) and 2,2,2-trichloroethylchloroformate (104.2 g.) is added dropwise to the stirred solution at 0° C. over a period of 0.5 hours. The mixture is stirred at 0° C. for a further 3 hours. The solids are filtered off and washed with acetone and the filtrate is evaporated to dryness. The resulting gum is taken up in chloroform (500 ml.) and washed with water (3×100 ml.). The chloroform solution is evaporated to dryness to give 2-(2,2,2-trichloroethoxycarbonylamino)ethanol; ν max (film), 3300, 2910, 1700, 1520, 1240, 1140, 1055, cm-1 ; δ (CDCl3) 3.43 (2H, t, J 7.5 Hz, HOCH2CH2NH--), 3.77 (2H, t, J 7.5 Hz, HOCH2CH2NH--) and 4.77 ppm (2H, s, --COOCH2CCl3).

Workup

  1. filtrationThe solids are filtered off
  2. washwashed with acetone
  3. customthe filtrate is evaporated to dryness
  4. washwashed with water (3×100 ml.)
  5. customThe chloroform solution is evaporated to dryness

Sources & evidence

ORD record
ord-1cf50f16440d429c85a4d160aa22816a
Source dataset
uspto-grants-1979_12
Patent number
US04180565

Reaction notes

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