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

HRID 1649365Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1649365
[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]

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-9a21761f63484d8faa5693dd9f8d5258
Quelldatensatz
uspto-grants-1983_11
Patentnummer
US04416889

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