Nitrogen → HCID 21487531, compound

HRID 1414448Notes

Reaction equation

HRID 1414448 reaction equation
N#N.[CH2:3]([C:5]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][CH3:13])[C:6]=1[NH2:7])[CH3:4].[CH2:14](Br)[C:15]#[CH:16].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH2:3]([C:5]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][CH3:13])[C:6]=1[NH:7][CH2:16][C:15]#[CH:14])[CH3:4]

Participants

6

Reactant 4

HCID 947NitrogenHCID 7842Propargyl bromideHCID 113692,6-DiethylanilineHCID 11430Potassium Carbonate2×

Product 1

HCID 21487531HCID 21487531, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A reactor equipped with a thermometer, stirrer, N2 inlet and outlet tubes and reflux condenser fitted with a drying tube is charged with 74.5 g (0.5 mole) of 2,6-diethylaniline, 71.4 g (0.6 mole) of propargyl bromide, 41.4 g (0.3 mole) of anhydrous potassium carbonate, and 125 ml of absolute ethanol. The mixture is refluxed for 18 hours under slight positive N2 pressure. The reaction mixture is cooled and additional potassium carbonate is added until the solution is weakly basic. It is then transferred to a separatory funnel. The supernatant organic layer which develops is isolated and dried over anhydrous potassium carbonate. The liquid is then separated by filtration and the solvent stripped in vacuo. The residue remaining is vacuum distilled. The clear liquid product (17.6 g) is approximately 90% pure 2,6-diethyl-N-propargylaniline as indicated by vapor phase chromatography. It has a boiling point of 86°-88° C at 0.6-0.7 mm Hg pressure. The impurities are 2,6-diethylaniline and 2,6-diethyl-N,N-dipropargylaniline.

Workup

  1. temperaturereflux condenser
  2. customfitted with a drying tube
  3. temperatureThe mixture is refluxed for 18 hours under slight positive N2 pressure
  4. temperatureThe reaction mixture is cooled
  5. customIt is then transferred to a separatory funnel
  6. customThe supernatant organic layer which develops is isolated
  7. dry with materialdried over anhydrous potassium carbonate
  8. customThe liquid is then separated by filtration
  9. distillationdistilled

Sources & evidence

ORD record
ord-127e82c56b9945ddba94f930435383aa
Source dataset
uspto-grants-1977_01
Patent number
US04001325

Reaction notes

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