Diethylenetriamine → 9-Decyl-1,4,7-triazecane-8,10-dione

HRID 2255349Notes

Reaction equation

HRID 2255349 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][NH2:26]>C(O)C>[CH2:1]([CH:11]1[C:12](=[O:14])[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 8111DiethylenetriamineHCID 19798168HCID 19798168, compound

Product 1

HCID 197981679-Decyl-1,4,7-triazecane-8,10-dioneYield 62.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A one litter round bottomed flask was charged with 0.076 mol (22.80 g) of ethyl α-decylmalonate (from above), 0.076 mol (7.74 g) diethylene triamine and 500 ml absolute ethanol. The mixture was refluxed for 42 days. During this period two ml aliquotes of solution were removed by hyperdermic 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 removed under reduced pressure and the product recrystallized from cold acetonitrile to yield 14.71 grams of a white heavy precipitate representing approximately a 62.1% conversion and having NMR characterizations in CDCL3, with signals reported in ppm downfield relative to TMS:

Workup

  1. temperatureThe mixture was refluxed for 42 days
  2. waitDuring this period two ml aliquotes of solution
  3. customwere removed by hyperdermic syringe on days 7,15,22, and 37 for NMR analysis
  4. customthe completeness of the reaction
  5. customAfter termination of the reflux, the ethanol was removed under reduced pressure
  6. customthe product recrystallized from cold acetonitrile

Sources & evidence

ORD record
ord-c445c65733934b8ea137a6c022b56db3
Source dataset
uspto-grants-1993_08
Patent number
US05240573

Reaction notes

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