Ammonia → N-BENZYLIDENE-2-PROPYNYLAMINE

HRID 1292540Notes

Reaction equation

HRID 1292540 reaction equation
CS(O[CH2:6][C:7]#[CH:8])(=O)=O.[CH:9](=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[NH3:17]>C1(C)C=CC=CC=1>[CH:9](=[N:17][CH2:6][C:7]#[CH:8])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 240BenzaldehydeHCID 305925propargyl mesylate

Product 1

HCID 4172560N-BENZYLIDENE-2-PROPYNYLAMINEYield 80%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Propargyl methanesulfonate (46.8 g, 0.35 mol) and benzaldehyde (47.0 g, 0.44 mol) were dissolved in 148 g of toluene and an aqueous 28% ammonia solution (180 g, 2.96 mol) was added dropwise at 24° C. over 7.5 hours to the solution, followed by stirring at the same temperature for 15 hours. After separating, the resultant organic phase was washed with water and concentrated to obtain 56.5 g of a crude product containing 40.0 g (yield: 80%) of N-benzylidene-2-propynylamine. The resulting crude product was distilled to obtain 34.9 g (purity: 97%, boiling point: 80°-83° C./2.5 mmHg) of N-benzylidene-2-propylamine.

Workup

  1. customAfter separating
  2. washthe resultant organic phase was washed with water
  3. concentrationconcentrated
  4. customto obtain 56.5 g of a crude product

Sources & evidence

ORD record
ord-a2f1271f7bb146ddb009283fd45d65be
Source dataset
uspto-grants-1998_05
Patent number
US05756769

Reaction notes

Loading…