Ammonia → N-BENZYLIDENE-2-PROPYNYLAMINE

HRID 1292542Notes

Reaction equation

HRID 1292542 reaction equation
[NH3:1].[CH:2](=O)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CS(O[CH2:15][C:16]#[CH:17])(=O)=O>C1(C)C=CC=CC=1>[CH:2](=[N:1][CH2:15][C:16]#[CH:17])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 240BenzaldehydeHCID 305925propargyl mesylate

Product 1

HCID 4172560N-BENZYLIDENE-2-PROPYNYLAMINE

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

An aqueous 28% ammonia solution (166.4 g, 2.74 mol) and benzaldehyde (30.6 g, 0.288 mol) were mixed and a solution prepared by dissolving propargyl methanesulfonate (36.7 g, 0.274 mol) in 147 g of toluene was added dropwise at 20°-25° C. over 3 hours to the solution, followed by stirring at the same temperature for 3 hours. After separating, the organic phase and aqueous phase were obtained. The organic phase obtained by washing the aqueous phase twice with 25 g of toluene was combined with the above organic phase and concentrated until the weight became 78 g to obtain a toluene solution of N-benzylidene-2-propynylamine.

Workup

  1. customa solution prepared
  2. additionwas added dropwise at 20°-25° C. over 3 hours to the solution
  3. customAfter separating
  4. customthe organic phase and aqueous phase were obtained
  5. customThe organic phase obtained
  6. washby washing the aqueous phase twice with 25 g of toluene
  7. concentrationconcentrated until the weight

Sources & evidence

ORD record
ord-f97151275f8f48e48ff2cf6411285c3d
Source dataset
uspto-grants-1998_05
Patent number
US05756769

Reaction notes

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