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

HRID 2285926Notes

Reaction equation

HRID 2285926 reaction equation
[C:1]1(C)[CH:6]=CC(S(OCC#C)(=O)=O)=C[CH:2]=1.[CH3:15][C:16]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:17]=1[NH2:18]>O>[CH3:15][C:16]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:17]=1[NH:18][CH2:6][C:1]#[CH:2]

Participants

4

Reactant 2

HCID 68962,6-DimethylanilineHCID 22547p-Toluenesulfonic acid, 2-propynyl ester

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Propargyl p-toluenesulphonate (6.0 g, 0.05 mole) was heated with 2,6-dimethylaniline (6.0 g, 0.05 mole) on steam bath for 2 hours, poured into water (100 ml), extracted into methylenedichloride (50 ml), dried (MgSO4), filtered, solvent evaporated and the product distilled to give 2,6-dimethylphenyl propargylamine, identical with that in Route II. Subsequent preparative steps were as outlined in Route II.

Workup

  1. extractionextracted into methylenedichloride (50 ml)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customsolvent evaporated
  5. distillationthe product distilled

Sources & evidence

ORD record
ord-617e5ce7239d41e781e7c9ef7186e8dc
Source dataset
uspto-grants-1982_04
Patent number
US04325966

Reaction notes

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