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Cesium carbonate → 2-Chloro-4-(5-ethyl-3,3-dimethyl-2,4-dioxopyrrolidin-1-yl)-3-methylbenzonitrile

HRID 1173558
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1173558
[Cl:1][C:2]1[C:9]([CH3:10])=[C:8](I)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH2:12]([CH:14]1[NH:18][C:17](=[O:19])[C:16]([CH3:21])([CH3:20])[C:15]1=[O:22])[CH3:13].C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[Cl:1][C:2]1[C:9]([CH3:10])=[C:8]([N:18]2[CH:14]([CH2:12][CH3:13])[C:15](=[O:22])[C:16]([CH3:21])([CH3:20])[C:17]2=[O:19])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 167319952-Chloro-4-iodo-3-methylbenzonitrileHCID 595570275-Ethyl-3,3-dimethylpyrrolidine-2,4-dione

Produkt 1

HCID 595568982-Chloro-4-(5-ethyl-3,3-dimethyl-2,4-dioxopyrrolidin-1-yl)-3-methylbenzonitrile
Ausbeute 27,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of 2-chloro-4-iodo-3-methylbenzonitrile (983 mg), 5-ethyl-3,3-dimethylpyrrolidine-2,4-dione (550 mg), cesium carbonate (1.73 g), tris(dibenzylideneacetone)dipalladium(0) (325 mg) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (615 mg) in dioxane was reacted in a microwave reactor at 120° C. for 5 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography and recrystallized from THF/hexane to give the title compound as a colorless solid (yield: 294 mg, 27%).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography
  6. customrecrystallized from THF/hexane

Quellen und Nachweise

ORD-Eintrag
ord-4f1a28a4428946deb87f769433539e70
Quelldatensatz
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07834051B2

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