Trichloroisocyanuric Acid → (2-Oxo-1,3-oxazolidin-3-yl)acetic acid

HRID 1711131Notes

Reaction equation

HRID 1711131 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:8][CH2:7][O:6][C:5]1=[O:9].C(=O)(O)[O-:11].[Na+].[Br-].[Na+].ClN1C(=O)N(Cl)C(=O)N(Cl)C1=O>CC(C)=O.CC1(C)N([O])C(C)(C)CCC1.C(O)(C)C>[O:9]=[C:5]1[N:4]([CH2:3][C:2]([OH:11])=[O:1])[CH2:8][CH2:7][O:6]1

Participants

8

Reactant 4

HCID 6909Trichloroisocyanuric AcidHCID 768872-Oxazolidinone, 3-(2-hydroxyethyl)-HCID 253881Sodium BromideHCID 516892Sodium Bicarbonate

Product 1

HCID 12676756(2-Oxo-1,3-oxazolidin-3-yl)acetic acidYield 70%

Reagents, catalysts & solvents 3

HCID 2724126TempoCatalystHCID 180AcetoneSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-(2-hydroxy-ethyl)-oxazolidin-2-one (0.575 g, 4.38 mmol) in acetone (40 ml) was added 15% aqueous sodium bicarbonate (12 ml) to give a white slurry, which was then cooled to 0° C. (JOC 2003, 68, 4999-5001). Sodium bromide (0.090 g, 0.88 mmol) and TEMPO (0.014 g, 0.09 mmol) were added and the resulting mixture was stirred for 10 minutes followed by the addition of trichloroisocyanuric acid (2.03 g, 8.76 mmol) in four equal portions added every five minutes. The pale yellow slurry was warmed to 25° C. and stirred for an additional 12 hours to yield a yellow solution. Iso-propanol (3 ml) was added and the mixture was stirred for 45 minutes to give a white slurry, which was filtered through a Celite® cake. The filtrate was concentrated in vacuo, quenched with saturated aqueous sodium bicarbonate and extracted with ethyl acetate (30 ml). The aqueous phase was acidified with 4N HCl until pH ˜2 and then put on for continuous extraction with methylene chloride (˜100 ml) for 16 hours. The organic extract was dried over sodium sulfate, filtered and concentrated in vacuo to yield (2-oxo-oxazolidin-3-yl)-acetic acid (0.445 g, 70%) as a pale yellow solid.

Workup

  1. customto give a white slurry, which
  2. additionadded every five minutes
  3. temperatureThe pale yellow slurry was warmed to 25° C.
  4. stirringstirred for an additional 12 hours
  5. customto yield a yellow solution
  6. stirringthe mixture was stirred for 45 minutes
  7. customto give a white slurry, which
  8. filtrationwas filtered through a Celite® cake
  9. concentrationThe filtrate was concentrated in vacuo
  10. customquenched with saturated aqueous sodium bicarbonate
  11. extractionextracted with ethyl acetate (30 ml)
  12. extractionput on for continuous extraction with methylene chloride (˜100 ml) for 16 hours
  13. extractionThe organic extract
  14. dry with materialwas dried over sodium sulfate
  15. filtrationfiltered
  16. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8fab61f3312e428186b9dd5a596ef727
Source dataset
uspto-grants-2010_09
Patent number
US07790747B2

Reaction notes

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