Dabco → 1-(3,4-Dichlorobenzyl)-3-cyano-6-methylpyrid-2-one

HRID 436705

Reaktionsgleichung

Reaktionsgleichung von HRID 436705
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[Cl:15])[CH2:5][NH:6][C:7](=[O:11])[CH2:8][C:9]#[N:10].CO[CH:18]=[CH:19][C:20](=O)[CH3:21].N12CCN(CC1)CC2>COCCO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[Cl:15])[CH2:5][N:6]1[C:20]([CH3:21])=[CH:19][CH:18]=[C:8]([C:9]#[N:10])[C:7]1=[O:11]

Komponenten

5

Edukt 3

HCID 9237DabcoHCID 942973-Buten-2-one, 4-methoxy-HCID 4168883N-(3,4-dichlorobenzyl)-2-cyanoacetamide

Produkt 1

HCID 203163511-(3,4-Dichlorobenzyl)-3-cyano-6-methylpyrid-2-oneAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80192-MethoxyethanolLösungsmittel

Versuchsvorschrift

A solution of 49.7 g. (0.204 mole) of N-(3,4-dichlorobenzyl)-2-cyanoacetamide, 48.0 g. (0.48 mole) of 4-methoxy-3-buten-2-one, and 4 g. of 1,4-diazabicyclo (2.2.2) octane (DABCO) in 160 ml. of 2-methoxyethanol is refluxed for 4 hr. The dark reaction mixture is then concentrated in vacuo and the crude solid is isolated by filtration from the resulting slurry and washed with ether. The crude product is dissolved in methylene chloride and the organic solution is washed with water, 2N-HCl and finally with more water. The methylene chloride is removed and the product is obtained in 62% yield by ether trituration.

Aufarbeitung

  1. customThe dark reaction mixture
  2. concentrationis then concentrated in vacuo
  3. customthe crude solid is isolated by filtration from the resulting slurry
  4. washwashed with ether
  5. dissolutionThe crude product is dissolved in methylene chloride
  6. washthe organic solution is washed with water, 2N-HCl and finally with more water
  7. customThe methylene chloride is removed
  8. customthe product is obtained in 62% yield by ether trituration

Quellen und Nachweise

ORD-Eintrag
ord-8676f4fd4901411d9d023b915b59605f
Quelldatensatz
uspto-grants-1977_06
Patentnummer
US04028084

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