2,6-Dimethylaniline → 2,6-dimethyl-N-prop-2-ynyl-aniline
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
Product 1
Reagents, catalysts & solvents 1
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
- extractionextracted into methylenedichloride (50 ml)
- dry with materialdried (MgSO4)
- filtrationfiltered
- customsolvent evaporated
- distillationthe product distilled
Sources & evidence
- ORD record
- ord-617e5ce7239d41e781e7c9ef7186e8dc
- Source dataset
- uspto-grants-1982_04
- Patent number
- US04325966
Reaction notes
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