Ethanol → 4-Chloro-4'-thiocyanatomethylbenzophenone

HRID 2102

Reaktionsgleichung

Reaktionsgleichung von HRID 2102
Br[CH2:2][C:3]1[CH:17]=[CH:16][C:6]([C:7]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)=[O:8])=[CH:5][CH:4]=1.[S-:18][C:19]#[N:20].[Na+].C(O)C>C(OCC)(=O)C>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([C:7]([C:6]2[CH:16]=[CH:17][C:3]([CH2:2][S:18][C:19]#[N:20])=[CH:4][CH:5]=2)=[O:8])=[CH:10][CH:11]=1

Komponenten

5

Edukt 3

HCID 702EthanolHCID 516871Sodium thiocyanateHCID 98396514-(4-Chlorobenzoyl)benzyl bromide

Produkt 1

HCID 187798994-Chloro-4'-thiocyanatomethylbenzophenoneAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

4-bromomethyl-4'-chlorobenzophenone (5.7 g) and sodium thiocyanate (5.5 g) were added to ethanol (50 ml), and the mixture was stirred for one hour at 60° C. The reaction mixture was concentrated, and water was added to the residue. The mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and then dried over anhydrous magnesium sulfate. Ethyl acetate was distilled off under reduced pressure. The residual solid was washed with a solvent mixture of n-hexane:ethyl acetate=10:1 to obtain the desired product (2.2 g, melting point: 129° to 131° C., yield:42%).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. additionwater was added to the residue
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationEthyl acetate was distilled off under reduced pressure
  7. washThe residual solid was washed with a solvent mixture of n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-39af67312f5442e6ae004f66e6de33ad
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05728699

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