Pyridine → 2,6-dimethyl-N-(2-furoyl)-N-propargyl-aniline

HRID 851483Notes

Reaction equation

HRID 851483 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[C:3]=1[NH:4][CH2:5][C:6]#[CH:7].N1C=CC=CC=1.[O:19]1[CH:23]=[CH:22][CH:21]=[C:20]1[C:24](Cl)=[O:25]>O1CCCC1>[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[C:3]=1[N:4]([C:24]([C:20]1[O:19][CH:23]=[CH:22][CH:21]=1)=[O:25])[CH2:5][C:6]#[CH:7]

Participants

5

Reactant 3

HCID 1049PyridineHCID 682422-Furancarbonyl chlorideHCID 2997052,6-dimethyl-N-prop-2-ynyl-aniline

Product 1

HCID 131504722,6-dimethyl-N-(2-furoyl)-N-propargyl-anilineYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

15.9 g (0.1 mol) of 2,6-dimethyl-N-propargylaniline and 8 g (0.1 mol) of pyridine were heated to the boil in 100 ml of tetrahydrofuran, and 13 g (0.1 mol) of furan-2-carboxylic acid chloride were added carefully. The reaction mixture was stirred under reflux for 15 minutes and then concentrated by distilling off the solvent in vacuo. The residue was taken up in methylene chloride and the methylene chloride mixture was washed with water. The organic phase was separated off, dried over sodium sulphate and concentrated. After triturating with petroleum ether, the residue crystallized. 22.5 g (89% of theory) of 2,6-dimethyl-N-(2-furoyl)-N-propargyl-aniline of melting point 109°-112° C. were obtained.

Workup

  1. temperatureunder reflux for 15 minutes
  2. concentrationconcentrated
  3. distillationby distilling off the solvent in vacuo
  4. washthe methylene chloride mixture was washed with water
  5. customThe organic phase was separated off
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated
  8. customAfter triturating with petroleum ether
  9. customthe residue crystallized

Sources & evidence

ORD record
ord-99ec2719e8ce4d6a8e8ef0b654369bc5
Source dataset
uspto-grants-1983_05
Patent number
US04385069

Reaction notes

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