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

HRID 422128

Reaction equation

HRID 422128 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

HCID 58294848O-3-methoxy-5-methylphenyl dimethylcarbamothioateYield 91.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-3123dddee2e9461a81930c4e3de5ee81
Source dataset
uspto-grants-2012_01
Patent number
US08101605B2

Linked notes

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