Bromine → 3-Bromo-5-chloromethyl-2-oxazolidinone

HRID 373157Notes

Reaction equation

HRID 373157 reaction equation
[Cl:1][CH2:2][CH:3]1[O:7][C:6](=[O:8])[NH:5][CH2:4]1.[Br:9]Br>[OH-].[Na+]>[Br:9][N:5]1[CH2:4][CH:3]([CH2:2][Cl:1])[O:7][C:6]1=[O:8]

Participants

4

Reactant 2

HCID 24408BromineHCID 908155-Chloromethyloxazolidin-2-one

Product 1

HCID 198119723-Bromo-5-chloromethyl-2-oxazolidinone

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

13.55 grams (0.1 mole) 5-chloromethyl-2-oxazolidinone, prepared in Example 1, were dissolved in 90 mL of a 1 M NaOH solution and then cooled to 0° C. 17.6 grams (0.11 moles) bromine were added dropwise, with stirring over a period of fifteen minutes. The product was extracted with methylene chloride. The extracts were then combined, dried and the solvent removed using a rotary evaporator to yield an orange solid. Proton NMR Data: δ3.15 (m, 1 proton), 3.48 (m, 1 proton), 3.7 (m, 2 protons), 4.7 (m, 1 proton) Elemental Analysis: Found (theory), C 24.05 (22.40), H 2.71 (2.35), N 6.98 (6.53), Cl 18.12 (16.53), Br 31.18 (37.26).

Workup

  1. extractionThe product was extracted with methylene chloride
  2. customdried
  3. customthe solvent removed
  4. customa rotary evaporator
  5. customto yield an orange solid

Sources & evidence

ORD record
ord-e35a62d96ace4a308f019d5e1c56664a
Source dataset
uspto-grants-1992_11
Patent number
US05162354

Reaction notes

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