Carbon Disulfide → 1,2-Bis(4-diethylamino-2-methylphenyl)ethane-1,2-dione

HRID 373732

Reaktionsgleichung

Reaktionsgleichung von HRID 373732
[Cl-].[Al+3].[Cl-].[Cl-].C(=S)=S.[CH2:8]([N:10]([CH2:18][CH3:19])[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[CH:12]=1)[CH3:9].[C:20](Cl)(=[O:24])[C:21](Cl)=[O:22]>C(Cl)(Cl)Cl.O>[CH2:18]([N:10]([CH2:8][CH3:9])[C:11]1[CH:16]=[CH:15][C:14]([C:20](=[O:24])[C:21]([C:14]2[CH:15]=[CH:16][C:11]([N:10]([CH2:18][CH3:19])[CH2:8][CH3:9])=[CH:12][C:13]=2[CH3:17])=[O:22])=[C:13]([CH3:17])[CH:12]=1)[CH3:19]

Komponenten

7

Edukt 4

HCID 6348Carbon DisulfideHCID 65578Oxalyl chlorideHCID 66679N,N-diethyl-m-toluidineHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 137821031,2-Bis(4-diethylamino-2-methylphenyl)ethane-1,2-dioneAusbeute 23,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6212ChloroformLösungsmittel2×

Versuchsvorschrift

To 8.3 g of anhydrous aluminum chloride, 30 ml of carbon disulfide was added, followed by dropwise addition of 16.3 g of N,N-diethyl-m-toluidine under ice-cooling. Then, 5 g of oxalyl chloride was added dropwise thereto at 5° C. or lower, and reacted for 1 hour with stirring. After the reaction, 50 ml of water and 100 ml of chloroform were added to the reaction solution. The chloroform layer obtained by separation was washed with 2N hydrochloric acid, dried and concentrated. The residue was recrystallized from ethyl acetate to yield 3.5 g of yellow 1,2-bis(4-diethylamino-2-methylphenyl)ethane-1,2-dione.

Aufarbeitung

  1. temperaturecooling
  2. customat 5° C. or lower, and reacted for 1 hour
  3. additionwere added to the reaction solution
  4. washwas washed with 2N hydrochloric acid
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was recrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-f940ba0a035943f89c458d4521051fe5
Quelldatensatz
uspto-grants-1992_11
Patentnummer
US05164512

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