Triethylenetetramine → HCID 19798169, compound

HRID 2255350Notes

Reaction equation

HRID 2255350 reaction equation
[CH2:1]([CH:11]([C:17]([O-:19])=O)[C:12]([O:14]CC)=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[NH2:20][CH2:21][CH2:22][NH:23][CH2:24][CH2:25][NH:26][CH2:27][CH2:28][NH2:29]>C(O)C>[CH2:1]([CH:11]1[C:12](=[O:14])[NH:29][CH2:28][CH2:27][NH:26][CH2:25][CH2:24][NH:23][CH2:22][CH2:21][NH:20][C:17]1=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

4

Reactant 2

HCID 5565TriethylenetetramineHCID 19798168HCID 19798168, compound

Product 1

HCID 19798169HCID 19798169, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A one liter round bottomed flask was charged with 0.053 mol (15.9 g) of ethyl n-decylmalonate, 0.053 mol (7.738 g) triethylene tetramine, and 500 ml absolute ethanol. During refluxing for 42 days, 2 ml aloquotes were removed by hypodermic syringe on days 7, 15, 22, and 37 for NMR analysis to determine the completeness of the reaction. After termination of the reflux the ethanol was distilled away and the product recrystallized from cold acetonitrile to yield 10.89 g of a very light fluffy white precipitate representing approximately a 60.0% conversion to the titled compound.

Workup

  1. temperatureDuring refluxing for 42 days
  2. custom2 ml aloquotes were removed by hypodermic syringe on days 7, 15, 22, and 37 for NMR analysis
  3. customthe completeness of the reaction
  4. distillationwas distilled away
  5. customthe product recrystallized from cold acetonitrile
  6. customto yield 10.89 g of a very light fluffy white precipitate

Sources & evidence

ORD record
ord-75c2cd3cc31d4f599d1ea3b917477ef7
Source dataset
uspto-grants-1993_08
Patent number
US05240573

Reaction notes

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