Ammonia → N-BENZYLIDENE-2-PROPYNYLAMINE

HRID 1292541Notes

Reaction equation

HRID 1292541 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 85%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Propargyl methanesulfonate (31.6 g, 0.236 mol) and benzaldehyde (31.9 g, 0.3 mol) were dissolved in 103 g of toluene and an aqueous 28% ammonia solution (122 g, 2 mol) was added dropwise at 21° C. over 8 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 until the weight became 57.3 g to obtain a toluene solution containing 28.6 g (yield: 85%) of N-benzylidene-2-propynylamine.

Workup

  1. customAfter separating
  2. washthe resultant organic phase was washed with water
  3. concentrationconcentrated until the weight
  4. customto obtain a toluene solution

Sources & evidence

ORD record
ord-5ddd84546c0b4594a50cd7d2ef279fcb
Source dataset
uspto-grants-1998_05
Patent number
US05756769

Reaction notes

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