Ammonia → HCID 11062644, compound

HRID 1292544Notes

Reaction equation

HRID 1292544 reaction equation
CS(O[CH2:6][C:7]#[C:8][CH3:9])(=O)=O.[CH:10](=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[NH3:18]>C1(C)C=CC=CC=1>[CH:10](=[N:18][CH2:6][C:7]#[C:8][CH3:9])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 240BenzaldehydeHCID 11051825HCID 11051825, compound

Product 1

HCID 11062644HCID 11062644, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-Butynyl methanesulfonate (18.7 g, 126 mol) and benzaldehyde (17.8 g, 168 mmol) were dissolved in 64 g of toluene and an aqueous 28% ammonia solution (68.1 g, 1.12 mol) was added dropwise at 23° C. over 3.5 hours to the solution, followed by stirring at the same temperature for 6 hours. After separating, the resulting organic phase was washed with water and concentrated to obtain 24.3 g of a crude product containing 17.4 g (yield: 88%) of N-benzylidene-2-butynylamine. To obtain 10.6 g (purity: 98%) of N-benzylidene-2-butynylamine, 17.3 g of this crude product was distilled off.

Workup

  1. customAfter separating
  2. washthe resulting organic phase was washed with water
  3. concentrationconcentrated
  4. customto obtain 24.3 g of a crude product

Sources & evidence

ORD record
ord-261130d3fe8045edb2f03b49dd0726b4
Source dataset
uspto-grants-1998_05
Patent number
US05756769

Reaction notes

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