Water → Cyano(phenyl)methyl benzenecarbodithioate

HRID 2055766Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2055766
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:9](=[S:11])=[S:10].Br[CH:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:14]#[N:15].O>C1COCC1>[C:9]([S:11][CH:13]([C:14]#[N:15])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[S:10])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 6348Carbon DisulfideHCID 22044Bromobenzyl CyanideHCID 178418255HCID 178418255, Verbindung

Produkt 1

HCID 58856295Cyano(phenyl)methyl benzenecarbodithioate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a 100 ml round bottom flask was added 5 ml phenyl magnesium bromide (3M solution in ethyl ether) and diluted to 20 ml with anhydrous THF. 1.2 g carbon disulfide was added dropwise to this mixture and stirred for ½ h at room temperature. Then to the dark red solution was added 3 g α-bromobenzeneacetonitrile dropwise and the mixture stirred for another 3 h. Water was added to the mixture and the organic product was extracted with diethyl ether (3×50 ml), dried with magnesium sulfate overnight and filtered. After removal of solvent and column chromatography (3:1 mixture of hexane and ethyl ether), pure α-cyanobenzyl dithiobenzoate was obtained as a red odorless solid (77% yield). Proton and carbon NMR spectra were consistent with the expected structure, CTA-CP-1.

Aufarbeitung

  1. stirringthe mixture stirred for another 3 h
  2. extractionthe organic product was extracted with diethyl ether (3×50 ml)
  3. dry with materialdried with magnesium sulfate overnight
  4. filtrationfiltered
  5. customAfter removal of solvent and column chromatography (3:1 mixture of hexane and ethyl ether)

Quellen und Nachweise

ORD-Eintrag
ord-c4a82de4b6af4941830ae04ac389ba3b
Quelldatensatz
uspto-grants-2008_02
Patentnummer
US07332552B2

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