Ethanolamine → HCID 86736911, compound

HRID 1164552Notes

Reaction equation

HRID 1164552 reaction equation
[CH3:1][CH:2]([C:15]1([O:20][CH2:19]1)[C:16]([OH:18])=O)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].C(N(CC)CC)C.ClC(OCC)=O.[CH2:34]([CH2:36][NH2:37])[OH:35]>C1COCC1>[OH:35][CH2:34][CH2:36][NH:37][C:16](=[O:18])[C:15]1([CH:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH3:1])[O:20][CH2:19]1

Participants

6

Reactant 4

HCID 700EthanolamineHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 86736910HCID 86736910, compound

Product 1

HCID 86736911HCID 86736911, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent4×

Procedure

To a solution of 0.2 g of 2-tetradecylglycidic acid (0.0007 mole) in 10 ml of anhydrous THF at 0° C. (ice water bath) with stirring is added 0.070 g of triethylamine (0.0007 mole) in a small amount of THF. The solution is stirred at 0° for 30 minutes and 76 mg of ethyl chloroformate (0.0007 mole) in a small amount of THF is added. The mixture is stirred at about 0° C. (ice water bath) for 3 hours (ppt. of Et3NHCl observed). At the end of 3 hours, 0.042 g (0.0007 mole) of ethanolamine in THF is added. The mixture is stirred at room temperature for 16 hours. The THF solvent is concentrated to about 1/3 its volume, water is added and the mixture extracted with ether. The ether extract is dried over Na2SO4 and the ether solvent removed to give a white solid of N-(2-hydroxyethyl)-2-tetradecylglycidamide which, upon recrystallization from acetone has a m.p. of 80°-82° C.

Workup

  1. stirringThe mixture is stirred at room temperature for 16 hours
  2. concentrationThe THF solvent is concentrated to about 1/3 its volume, water
  3. additionis added
  4. extractionthe mixture extracted with ether
  5. extractionThe ether extract
  6. dry with materialis dried over Na2SO4
  7. customthe ether solvent removed

Sources & evidence

ORD record
ord-08171971df564943a3983a88feab4a22
Source dataset
uspto-grants-1983_01
Patent number
US04370343

Reaction notes

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