Bromine → 3-Bromo-4,4-dimethyloxazolidin-2-one

HRID 436530Notes

Reaction equation

HRID 436530 reaction equation
[CH3:1][C:2]1([CH3:8])[CH2:6][O:5][C:4](=[O:7])[NH:3]1.[Br:9]Br>[OH-].[Na+]>[Br:9][N:3]1[C:2]([CH3:8])([CH3:1])[CH2:6][O:5][C:4]1=[O:7]

Participants

4

Reactant 2

HCID 24408BromineHCID 1413154,4-Dimethyl-1,3-oxazolidin-2-one

Product 1

HCID 945953-Bromo-4,4-dimethyloxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

12.3 g (0.11 mol) 4,4-dimethyl-2-oxazolidinone was dissolved in 180 ml of 1 M sodium hydroxide and the resulting solution was cooled to 0°. 19.2 g (0.012 mol) bromine was added dropwise with stirring over 0.25 hr and the reaction mixture was stirred at 0° for an additional 0.75 hr. The N-bromamine separated from the reaction mixture as an orange colored solid. The solid was isolated by filtration and thoroughly washed with cold water. Trituration of this material in petroleum ether (30°-60°) gave 16.2 g (0.084 mol), 76%, 3-bromo-4,4-dimethyl-2-oxazolidinone (NBDMO), mp 118°-120°; uv (H2O) λmax 274 nm, ε= 201 M-1 cm-1 ; ir (KBr): 2985, 1725, 1370, 1290, 1200, 1165, 1040 and 740 cm-1 ; pmr (CDCl3) δ 4.27 (s, 2H) and 1.33 (s, 6H) ppm.

Workup

  1. temperaturethe resulting solution was cooled to 0°
  2. stirringthe reaction mixture was stirred at 0° for an additional 0.75 hr
  3. customThe N-bromamine separated from the reaction mixture as an orange colored solid
  4. customThe solid was isolated by filtration
  5. washthoroughly washed with cold water

Sources & evidence

ORD record
ord-03d3fe2baf1b4665aeaf91f3bce9da99
Source dataset
uspto-grants-1977_02
Patent number
US04009178

Reaction notes

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