2,6-Dimethylaniline → 2,6-dimethyl-N-prop-2-ynyl-aniline

HRID 2285925Notes

Reaction equation

HRID 2285925 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH2:4].[CH2:10](Cl)[C:11]#[CH:12].[OH-].[Na+]>>[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH:4][CH2:12][C:11]#[CH:10]

Participants

4

Reactant 3

HCID 68962,6-DimethylanilineHCID 122213-Chloro-1-propyneHCID 14798Sodium Hydroxide

Product 1

HCID 2997052,6-dimethyl-N-prop-2-ynyl-aniline

Procedure

2,6-Dimethylaniline (12.1 g, 0.1 mole) and propargyl chloride (3.8 g, 0.05 mole), were mixed and heated over a steam bath using an efficient reflux condenser for 8 hours, then treated with aqueous caustic soda solution, extracted with ether, the ethereal layer worked up and the residue distilled to give 2,6-dimethylphenyl propargylamine, b.p. 56°-58° C./0.01 mm.

Workup

  1. temperatureheated over a steam bath
  2. customfor 8 hours
  3. extractionextracted with ether
  4. distillationthe residue distilled

Sources & evidence

ORD record
ord-7661514d518048dea3530dbd0da51e0c
Source dataset
uspto-grants-1982_04
Patent number
US04325966

Reaction notes

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