Ethylenediamine → N-(6,6-dimethyl-2,4-heptadiynyl)ethylenediamine

HRID 1654234Notes

Reaction equation

HRID 1654234 reaction equation
[CH2:1]([NH2:4])[CH2:2][NH2:3].[CH3:5][C:6]([CH3:14])([CH3:13])[C:7]#[C:8][C:9]#[C:10][CH2:11]Br>C(O)C>[CH3:5][C:6]([CH3:14])([CH3:13])[C:7]#[C:8][C:9]#[C:10][CH2:11][NH:3][CH2:2][CH2:1][NH2:4]

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 193901786,6-Dimethyl-2,4-heptadiynyl bromide

Product 1

HCID 20079885N-(6,6-dimethyl-2,4-heptadiynyl)ethylenediamineYield 63%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 20 ml of ethanol was dissolved 1.5 g of ethylenediamine. Then 1.24 g of 6,6-dimethyl-2,4-heptadiynyl bromide was added to the solution followed by stirring at room temperature overnight. The solvent was distilled off under reduced pressure and the residue was extracted with ethyl ether and saturated sodium bicarbonate aqueous solution. After the organic layer was taken by fractionation, the aqueous layer was further extracted with ethyl ether. The procedure was repeated 5 times and the ethereal layer was dried over anhydrous magnesium sulfate. The drying agent was filtered off and the solvent was then removed under reduced pressure to give 695 mg (yield: 63%) of N-(6,6-dimethyl-2,4-heptadiynyl)ethylenediamine as light yellow oil.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. extractionthe residue was extracted with ethyl ether and saturated sodium bicarbonate aqueous solution
  3. extractionthe aqueous layer was further extracted with ethyl ether
  4. dry with materialthe ethereal layer was dried over anhydrous magnesium sulfate
  5. filtrationThe drying agent was filtered off
  6. customthe solvent was then removed under reduced pressure

Sources & evidence

ORD record
ord-96febfc75e9e4bd8a853019fd73cbdc4
Source dataset
uspto-grants-1995_04
Patent number
US05405873

Reaction notes

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