Dimethylthiocarbamoyl chloride → 2-methoxy-N,N-dimethyl-2-(2-pyridyl)thioacetamide

HRID 1076375Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1076375
C1([Li])C=CC=CC=1.C1C=CC=CC=1.CCOCC.[CH3:19][O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1.[CH3:28][N:29]([CH3:33])[C:30](Cl)=[S:31]>O.C1C=CC=CC=1>[CH3:19][O:20][CH:21]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1)[C:30]([N:29]([CH3:33])[CH3:28])=[S:31]

Komponenten

7

Edukt 4

HCID 27871Dimethylthiocarbamoyl chlorideHCID 2532202-(Methoxymethyl)pyridineHCID 22174802Benzene etherHCID 178506676HCID 178506676, Verbindung

Produkt 1

HCID 155819592-methoxy-N,N-dimethyl-2-(2-pyridyl)thioacetamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittel2×HCID 962WaterLösungsmittel

Versuchsvorschrift

To 0.10 mole of phenyl lithium in 100 ml. of benzene/ether at 0°C. is added dropwise 10.6 g. (0.084 mole) of 2-(methoxymethyl)pyridine dissolved in 75 ml. of benzene. To this mixture is added dropwise 10.0 g. (0.081 mole) of N,N-dimethylthiocarbamoyl chloride in 100 ml. of benzene. The resulting mixture is stirred at room temperature overnight, then poured into 100 ml. of water and acidified. The organic phase is extracted once with dilute aqueous acid. The combined aqueous phases are extracted twice with ether, then made basic to about pH 10 and extracted three times with chloroform. The combined chloroform extracts are dried over magnesium sulfate and the solvent is removed by evaporation. The residue is chromatographed, then distilled in vacuo to give 2-methoxy-N,N-dimethyl-2-(2-pyridyl)thioacetamide.

Aufarbeitung

  1. additionTo this mixture is added dropwise 10.0 g
  2. additionpoured into 100 ml
  3. extractionThe organic phase is extracted once with dilute aqueous acid
  4. extractionThe combined aqueous phases are extracted twice with ether
  5. extractionextracted three times with chloroform
  6. dry with materialThe combined chloroform extracts are dried over magnesium sulfate
  7. customthe solvent is removed by evaporation
  8. customThe residue is chromatographed
  9. distillationdistilled in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-8dced8367e834f5994f43cd105609757
Quelldatensatz
uspto-grants-1976_05
Patentnummer
US03956494

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