Pyridine → 4-Chloromethyl-4-methyl-oxazolidin-2-one

HRID 1023477Notes

Reaction equation

HRID 1023477 reaction equation
O[CH2:2][C:3]1([CH3:9])[CH2:7][O:6][C:5](=[O:8])[NH:4]1.S(Cl)([Cl:12])=O.N1C=CC=CC=1>ClCCCl>[Cl:12][CH2:2][C:3]1([CH3:9])[CH2:7][O:6][C:5](=[O:8])[NH:4]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 245546Nsc57599

Product 1

HCID 553038834-Chloromethyl-4-methyl-oxazolidin-2-oneYield 71%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
110 °C

Procedure

To a suspension of 4-(hydroxymethyl)-4-methyloxazolidin-2-one (1.89 g, 14.4 mmol) in 1,2-dichloroethane (10 ml) was added thionyl chloride (5.0 ml, 69 mmol) dropwise over 10 min. Pyridine (5.0 ml, 62 mmol) was added, and the solution heated to 110° C. for 2 h. The solution was cooled to RT, concentrated, and the residue purified by flash chromatography (30%→100% EtOAc in hexanes) to give the title compound as a white solid (1.52 g, 10.2 mmmol, 71%). 1H NMR (CDCl3, 400 MHz) δ 1.49 (s, 3H), 3.55 (s, 2H), 4.12 (d, J=9.2 Hz, 1H), 4.33 (d, 8.8 Hz, 1H), 5.8 (br s, 1H). ESI/APCI calculated for C5H8ClNO2: 149.02. Found: 150 (MH+).

Workup

  1. temperatureThe solution was cooled to RT
  2. concentrationconcentrated
  3. customthe residue purified by flash chromatography (30%→100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-ee745defa60d4c138466dc9dca885735
Source dataset
uspto-grants-2014_05
Patent number
US08722715B2

Reaction notes

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