Ammonia → HCID 18915581, compound

HRID 1292545Notes

Reaction equation

HRID 1292545 reaction equation
CS(O[CH2:6][C:7]#[C:8][C:9]1[S:10][CH:11]=[CH:12][CH:13]=1)(=O)=O.[CH:14](=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[NH3:22]>C1(C)C=CC=CC=1>[CH:14](=[N:22][CH2:6][C:7]#[C:8][C:9]1[S:10][CH:11]=[CH:12][CH:13]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 240BenzaldehydeHCID 142310232-Propyn-1-ol, 3-(2-thienyl)-, 1-methanesulfonate

Product 1

HCID 18915581HCID 18915581, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-(2-Thienyl)-2-propynyl methanesulfonate (2.47 g, 11.4 mmol) and benzaldehyde (1.51 g, 14.3 mmol) were dissolved in 15.9 g of toluene and an aqueous 28% ammonia solution (5.89 g, 97 mol) was added dropwise at 23° C. over one hour to the solution, followed by stirring at the same temperature for 22 hours. After separating, the resultant organic phase was washed with water and concentrated to obtain 18.7 g of a toluene solution containing 1.49 g (yield: 60%) of N-benzylidene-3-(2-thienyl)-2-propynylamine.

Workup

  1. customAfter separating
  2. washthe resultant organic phase was washed with water
  3. concentrationconcentrated
  4. customto obtain 18.7 g of a toluene solution

Sources & evidence

ORD record
ord-d91832a4229848f282a41ca6474b72f8
Source dataset
uspto-grants-1998_05
Patent number
US05756769

Reaction notes

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