Water → 5-(4-Chlorobutyl)-3-(1-methylethyl)-2-oxazolidinone

HRID 373011Notes

Reaction equation

HRID 373011 reaction equation
[C:1]([Cl:4])(Cl)=O.[CH3:5][CH:6]([NH:8][CH2:9][CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][O:11]1)[CH3:7].C(N(CC)CC)C.[OH2:23]>C1(C)C=CC=CC=1.[Cl-].[Zn+2].[Cl-]>[Cl:4][CH2:1][CH2:13][CH2:14][CH2:15][CH:10]1[O:11][C:12](=[O:23])[N:8]([CH:6]([CH3:7])[CH3:5])[CH2:9]1

Participants

7

Reactant 4

HCID 962WaterHCID 6371PhosgeneHCID 8471TriethylamineHCID 239652HCID 239652, compound

Product 1

HCID 198114795-(4-Chlorobutyl)-3-(1-methylethyl)-2-oxazolidinoneYield 81%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalyst2×HCID 1140TolueneSolvent3×

Procedure

A solution of phosgene (287 mL of a 20% solution, 273 g, 0.55 mol) in toluene and additional toluene (100 mL) was cooled to -10° C. by an ice/methanol bath and a solution of tetrahydro-N-(1-methylethyl)-2H-pyran-2-methanamine (41.13 g, 0.262 mol) and triethylamine (27.9 g, 0.276 mol) in toluene (300 mL) was added dropwise, keeping the temperature below 5° C. The mixture was warmed to room temperature and refluxed under nitrogen for 30 min. Zinc chloride (0.65 g) was added and refluxing was continued for 15 min. An additional portion of zinc chloride (0.32 g) was added, and the mixture was refluxed for 24 hr and allowed to stand at room temperature for several days. Water (750 mL) was added, and the layers were separated. The organic layer was washed twice again with water and once with a saturated sodium chloride solution, dried (magnesium sulfate), treated with charcoal, filtered, and evaporated to an oil. The oil was distilled under reduced pressure, and the fraction distilling from 148°-165° C./0.3 mm was collected to give 46.7 g (81% yield).

Workup

  1. customthe temperature below 5° C
  2. temperaturerefluxed under nitrogen for 30 min
  3. temperaturerefluxing
  4. temperaturethe mixture was refluxed for 24 hr
  5. waitto stand at room temperature for several days
  6. customthe layers were separated
  7. washThe organic layer was washed twice again with water and once with a saturated sodium chloride solution
  8. dry with materialdried (magnesium sulfate)
  9. additiontreated with charcoal
  10. filtrationfiltered
  11. customevaporated to an oil
  12. distillationThe oil was distilled under reduced pressure
  13. distillationthe fraction distilling from 148°-165° C./0.3 mm
  14. customwas collected
  15. customto give 46.7 g (81% yield)

Sources & evidence

ORD record
ord-9c961b12f98b4eabbbdbdd86e93005ef
Source dataset
uspto-grants-1992_11
Patent number
US05162322

Reaction notes

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