Ethanolamine → N,N'-bis(2-hydroxyethyl)-trans-2-dodecenediamide

HRID 1603964Notes

Reaction equation

HRID 1603964 reaction equation
[C:1]([OH:16])(=O)/[CH:2]=[CH:3]/[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=O.C([N:19]([CH2:22][CH3:23])CC)C.C([O:28]C(Cl)=O)C(C)C.[CH2:32]([CH2:34][NH2:35])[OH:33]>C1COCC1>[OH:33][CH2:32][CH2:34][NH:35][C:1](=[O:16])/[CH:2]=[CH:3]/[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([NH:19][CH2:22][CH2:23][OH:28])=[O:14]

Participants

6

Reactant 4

HCID 700EthanolamineHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 5283028Traumatic Acid

Product 1

HCID 19606627N,N'-bis(2-hydroxyethyl)-trans-2-dodecenediamideYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-10 °C

Procedure

A mixture of traumatic acid (4.57 g; 20 mmol) and triethylamine (4.26 g; 42 mmol) in anhydrous THF (150 ml) allowed to stir at -10° C., was dropwide added, over a period of 30 min, with a solution of isobutylchloroformate (5.74 g; 42 mmol) in THF (50 ml). The mixture was stirred at -10° C. for 2 hrs and at 0° C. for additional 15 hrs and added dropwise, over a period of 30 min, with ethanolamine (3.5 g). After stirring for additional 6 hrs at 0° C., the resulting suspension was filtered. The filtrate was discarded and the solid was dried under vacuum. The crude product obtained was crystallized from water (100 ml). The crystalline fraction was separated by filtration, washed three times with water (20 ml) and finally dried in high vacuo.

Workup

  1. stirringThe mixture was stirred at -10° C. for 2 hrs and at 0° C. for additional 15 hrs
  2. stirringAfter stirring for additional 6 hrs at 0° C.
  3. filtrationthe resulting suspension was filtered
  4. customthe solid was dried under vacuum

Sources & evidence

ORD record
ord-f05169b7cafe4735aed91f9c0f8b5c5e
Source dataset
uspto-grants-1999_11
Patent number
US05990170

Reaction notes

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