Triethylamine → Ethyl (2Z)-2-((2,6-dichloropyridin-3-yl)carbonyl)-3-(dimethylamino)prop-2-enoate

HRID 1696934Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1696934
[Cl:1][C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].CN[C:14]([NH:21][CH3:22])=[CH:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].[CH2:23](N(CC)CC)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:3]([C:4](/[C:15](=[CH:14]/[N:21]([CH3:22])[CH3:23])/[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[O:5])=[CH:7][CH:8]=[C:9]([Cl:11])[N:10]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 122639842,6-Dichlorpyridine-3-carbonyl chlorideHCID 85819813Ethyl 3,3-dimethylaminoacrylate

Produkt 1

HCID 15675736Ethyl (2Z)-2-((2,6-dichloropyridin-3-yl)carbonyl)-3-(dimethylamino)prop-2-enoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of 2,6-dichloronicotinoyl chloride (62.5 g), ethyl 3,3-dimethylaminoacrylate (58.8 g) and triethylamine (69 g) in toluene (600 mL) was stirred at 90° C. for 1 hour then cooled and concentrated. The concentrate was dissolved in dichloromethane (60 mL), diluted with diethyl ether, and filtered. The filtrate was concentrated, and the concentrate was crystallized from dichloromethane/diethyl ether/hexanes.

Aufarbeitung

  1. temperaturethen cooled
  2. concentrationconcentrated
  3. dissolutionThe concentrate was dissolved in dichloromethane (60 mL)
  4. additiondiluted with diethyl ether
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. customthe concentrate was crystallized from dichloromethane/diethyl ether/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-59468fef94ac434f8f11f2f60a94b9e2
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163769B2

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