Diethyl Ether → O-3-methoxy-5-methylphenyl dimethylcarbamothioate

HRID 422128

Reaktionsgleichung

Reaktionsgleichung von HRID 422128
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:10])[CH:6]=[C:7]([CH3:9])[CH:8]=1.N12CCN(CC1)CC2.[CH3:19][N:20]([CH3:24])[C:21](Cl)=[S:22].CCOCC>CN(C=O)C>[CH3:19][N:20]([CH3:24])[C:21](=[S:22])[O:10][C:5]1[CH:6]=[C:7]([CH3:9])[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1

Komponenten

6

Edukt 4

HCID 3283Diethyl EtherHCID 9237DabcoHCID 27871Dimethylthiocarbamoyl chlorideHCID 766743-Methoxy-5-Methylphenol

Produkt 1

HCID 58294848O-3-methoxy-5-methylphenyl dimethylcarbamothioateAusbeute 91,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a mixture of 3-methoxy-5-methylphenol (7) (3.39 g, 24.5 mmol) and 1,4-diazabicyclo[2.2.2]octane (5.50 g, 49.0 mmol) in DMF (20 mL) was added dimethylthiocarbamoyl chloride (8) (6.06 g, 49.0 mmol) portionwise. The reaction mixture was stirred at room temperature overnight and 500 mL of ether was added. The organics were washed with water (150 mL), brine (2×50 mL), dried (Na2SO4), and concentrated. Purification by chromatography on silica gel (Hexanes/EtOAc, 4:1) gave O-3-methoxy-5-methylphenyl dimethylcarbamothioate (9) (5.05 g, 91%) as a colourless solid.

Aufarbeitung

  1. washThe organics were washed with water (150 mL), brine (2×50 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customPurification by chromatography on silica gel (Hexanes/EtOAc, 4:1)

Quellen und Nachweise

ORD-Eintrag
ord-3123dddee2e9461a81930c4e3de5ee81
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101605B2

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