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Chemical Structure| 598-42-5 Chemical Structure| 598-42-5

Structure of 598-42-5

Chemical Structure| 598-42-5

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Product Details of [ 598-42-5 ]

CAS No. :598-42-5
Formula : C2H5NO2
M.W : 75.07
SMILES Code : OCC(N)=O
MDL No. :MFCD00047895
InChI Key :TZGPACAKMCUCKX-UHFFFAOYSA-N
Pubchem ID :69021

Safety of [ 598-42-5 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 598-42-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 598-42-5 ]

[ 598-42-5 ] Synthesis Path-Downstream   1~4

  • 2
  • [ 598-42-5 ]
  • [ 105-58-8 ]
  • [ 2346-26-1 ]
YieldReaction ConditionsOperation in experiment
55% With potassium tert-butylate; In methanol; at 75℃; for 18h;Inert atmosphere; [00227] A solution of glycolamide (2.10 g, 28 mmol), diethylcarbonate (4.06 mL, 34.0 mmol), and KOtBu (3.14 g, 28 mmol) in MeOH (30 mL) was heated to 75C for 18 h under N2 gas. The mixture was cooled to rt and concentrated under reduced pressure. The residue was diluted in a mixture of brine (100 mL) and 1M HCl (100 mL), and the aq phase was extracted with EtOAc (3X50 mL). The combined organic phases were dried over MgS04, filtered, and concentrated under reduced pressure to provide oxazolidine-2,4-dione as a solid (1.56 g, 55%). 1H NMR (300 MHz, DMSO) delta 11.8 (s, 1H), 4.75 (s, 2H)._
With potassium tert-butylate; In methanol;Heating / reflux; To a solution of glycolamide (14 g, 186 mmol) and diethyl carbonate (27.1 mL, 224 mmol) in methanol (200 mL) was added potassium t-butoxide (20.8 g, 186 mmol). The reaction mixture was refluxed overnight, then cooled to room temperature. The solvent was removed in vacuo. The residue was dissolved in brine, acidified with 2N HCl, then extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo to give 8.0 g of oxazolidinedione as a white solid.
With sodium methylate; In methanol; for 1.5h;Reflux; Step A: Oxazolidine-2,4-dione; To a solution of NaOMe (1.05 mmoles) in MeOH (21 ml) there are added 2-hydroxyacetamide (1 mmole) and diethyl carbonate (1.15 mmoles), and the reaction mixture is then heated at reflux for 1.5 hours. The reaction mixture is evaporated to dryness and then taken up in water. The aqueous phase is extracted with diethyl ether. The aqueous phase is acidified (pH 2) and then evaporated to dryness. The residue is triturated in AcOEt and filtered. The product obtained is purified on silica gel (c-Hexane/AcOEt; 1/1) to yield the title product in the form of a white powder.
With potassium tert-butylate; In methanol; for 20h;Reflux; Step 1 Oxazolidine-2,4-dione 2-Hydroxyacetamide (2.0 g, 26.6 mmol) and potassium tert-butoxide (3.0 g, 26.6 mmol) were dissolved in dry methanol (50 mL), added with diethyl carbonate (3.8 g, 31.9 mmol) and stirred at reflux for 20 hours. The reaction solution was cooled, concentrated under reduced pressure, dissolved in water and acidified to pH=2 with 6M hydrochloric acid solution. The mixture was extracted with ethyl acetate (100 mL*3), and the organic layer was washed with saturated brine and water, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure to give oxazolidine-2,4-dione (1.2 g, crude product). 1H NMR (400 MHz, DMSO) 4.75 (s, 2H), 3.91 (s, 1H).

  • 3
  • [ 71-36-3 ]
  • ammonium glycolate [ No CAS ]
  • [ 598-42-5 ]
  • [ 7397-62-8 ]
  • 4
  • [ 335349-57-0 ]
  • [ 598-42-5 ]
  • C8H8IN3O4 [ No CAS ]
 

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