Thionyl Chloride → HCID 91618549, compound

HRID 595251Notes

Reaction equation

HRID 595251 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][CH:7]1[O:11][C:10](=[O:12])[NH:9][C:8]1([CH3:14])[CH3:13]>N1C=CC=CC=1>[Cl:3][CH2:6][CH:7]1[O:11][C:10](=[O:12])[NH:9][C:8]1([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 67508214HCID 67508214, compound

Product 1

HCID 91618549HCID 91618549, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
60 °C

Procedure

Thionyl chloride (0.13 ml, 1.72 mmol) was added to a mixture of 5-(hydroxymethyl)-4,4-dimethyloxazolidin-2-one (50 mg, 0.34 mmol) in pyridine (1 mL) at −20° C. The mixture was allowed to stir for 15 minutes and then warmed to 60° C. for 1 hour. The mixture was concentrated under reduced pressure and the residue was purified by column chromatography on silica (20-100% ethyl acetate/hexanes) to afford 5-(chloromethyl)-4,4-dimethyloxazolidin-2-one. 1H NMR (500 MHz, CDCl3) δ 6.20 (br s, 1H), 4.38-4.35 (m, 1H), 3.75-3.70 (m, 1H), 3.62-3.57 (m, 1H), 1.42 (s, 3H), 1.31 (s, 3H).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue was purified by column chromatography on silica (20-100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-bb1c1e5b48af4d9f91bc548229a1584b
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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