Ethyl Acetate → HCID 86665537, compound

HRID 1770729Notes

Reaction equation

HRID 1770729 reaction equation
Cl[CH2:2][C:3]1([CH3:9])[CH2:7][O:6][C:5](=[O:8])[NH:4]1.[C:10]([O-:13])(=[S:12])[CH3:11].[K+].C(OCC)(=O)C>CN(C)C=O>[C:10](=[O:13])([S:12][CH2:2][C:3]1([CH3:9])[CH2:7][O:6][C:5](=[O:8])[NH:4]1)[CH3:11]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 23670855Potassium ethanethioateHCID 553038834-Chloromethyl-4-methyl-oxazolidin-2-one

Product 1

HCID 86665537HCID 86665537, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 4-(chloromethyl)-4-methyloxazolidin-2-one (10.22 g, 68.32 mmol) in N,N-dimethylformamide (100 ml) was added potassium thioacetate (9.07 g, 79.6 mmol). The suspension was heated to 90° C. for 18 hour, cooled to room temperature, and concentrated in vacuo. The residue was suspended in 400 ml ethyl acetate, washed three times with 100 ml saturated NaHCO3, 100 ml saturated NaCl, dried on MgSO4, and concentrated in vacuo. Flash chromatography (30% to 100% ethyl acetate in hexanes) afforded the title compound as a yellow oil (6.07 g, 31.2 mmol, 46%). 1H NMR (CDCl3, 400 MHz) δ 1.45 (s, 3H), 2.42 (s, 3H), 3.07 (d, J=14.0 Hz, 1H), 3.21 (d, J=14.0 Hz, 1H), 4.08 (d, J=8.8 Hz, 1H), 4.15 (d, J=8.8 Hz, 1H), 5.59 (br s, 1H); LRMS (ESI/APCI) m/z 190 [M+H]+.

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated in vacuo
  3. washwashed three times with 100 ml saturated NaHCO3, 100 ml saturated NaCl
  4. customdried on MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3ff1f2b885de47b6a48bdee2339dd81c
Source dataset
uspto-grants-2016_02
Patent number
US09248117B2

Reaction notes

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