Sulfuric Acid → HCID 11378760, compound

HRID 1514033Notes

Reaction equation

HRID 1514033 reaction equation
[CH3:1][CH:2]1[CH2:6][O:5][C:4](=[O:7])[NH:3]1.[H-].[Na+].I[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].OS(O)(=O)=O>C1COCC1.CCCCCC>[CH3:1][CH:2]1[CH2:6][O:5][C:4](=[O:7])[N:3]1[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 123351-IodopentaneHCID 24758Sodium hydrideHCID 98554554-Methyl-1,3-oxazolidin-2-one

Product 1

HCID 11378760HCID 11378760, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

4-Methyl-oxazolidin-2-one (18.0 g, 178 mmol) in THF (100 ml) was added slowly via dropping funnel to a slurry of hexane-washed NaH (60% in mineral oil, 7.12 g, 178 mmol, 1.0 quiv.) in THF (400 ml) upon which H2-evolution was observed. Neat iodopentane (70.51 g, 356 mmol, 2.0 equiv.) was added rapidly and the mixture stirred for 1 h at room temperature, then heated to reflux for 60 h. After cooling to 5° C., 2N H2SO4 (180 ml) was slowly added. The mixture was extracted with MTBE and worked up as usual. Distillation over a Widmer-column at 115° C./0.08 mbar afforded the product as a slightly yellow liquid (20.54 g, 73%).

Workup

  1. temperatureheated
  2. temperatureto reflux for 60 h
  3. temperatureAfter cooling to 5° C.
  4. extractionThe mixture was extracted with MTBE
  5. distillationDistillation over a Widmer-column at 115° C./0.08 mbar

Sources & evidence

ORD record
ord-22daa02fd59d47d48faaefde9cadde24
Source dataset
uspto-grants-2012_07
Patent number
US08222200B2

Reaction notes

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