Potassium Hydroxide → 4,4-Dimethyl-2-[(2,4,5-trichlorophenyl)methyl]-1,2-oxazolidin-3-one

HRID 1995494Notes

Reaction equation

HRID 1995494 reaction equation
[OH-].[K+].[CH3:3][C:4]1([CH3:10])[CH2:8][O:7][NH:6][C:5]1=[O:9].[Cl:11][C:12]1[CH:17]=[C:16]([Cl:18])[C:15]([Cl:19])=[CH:14][C:13]=1[CH2:20]Br>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>[Cl:11][C:12]1[CH:17]=[C:16]([Cl:18])[C:15]([Cl:19])=[CH:14][C:13]=1[CH2:20][N:6]1[C:5](=[O:9])[C:4]([CH3:10])([CH3:3])[CH2:8][O:7]1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 6421514,4-Dimethyl-1,2-oxazolidin-3-oneHCID 139449891-(Bromomethyl)-2,4,5-trichlorobenzene

Product 1

HCID 131925704,4-Dimethyl-2-[(2,4,5-trichlorophenyl)methyl]-1,2-oxazolidin-3-oneYield 19.9%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred suspension of 1.9 grams (0.029 mole) of crushed 85% pure potassium hydroxide and 1.7 grams (0.005 mole) of tetrabutylammonium bromide in 20 ml of tetrahydrofuran was added dropwise a solution of 3.0 grams (0.026 mole) of 4,4-dimethyl-3-isoxazolidinone (Example 30, Step B) and 7.1 grams (0.026 mole) of (2,4,5-trichlorophenyl)methyl bromide in 50 ml of tetrahydrofuran. The addition required one hour. Upon completion of addition the reaction mixture was stirred at ambient temperature for 1.5 hours and then filtered. The filtrate was diluted with 150 ml of methylene chloride and washed with three 75-ml portions of water. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to give an oil residue. The oil was subjected to column chromatography on silica gel. Elution was accomplished using 10% ethyl acetate in heptane. The appropriate fractions were combined and concentrated under reduced pressure to give 1.6 grams of 2-[(2,4,5 -trichlorophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone as an oil.

Workup

  1. additionThe addition required one hour
  2. additionUpon completion of addition the reaction mixture
  3. filtrationfiltered
  4. additionThe filtrate was diluted with 150 ml of methylene chloride
  5. washwashed with three 75-ml portions of water
  6. dry with materialThe organic layer was dried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customto give an oil residue
  10. washElution
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1a31c416f72a4992bb846f2ee9a63d79
Source dataset
uspto-grants-1983_09
Patent number
US04405357

Reaction notes

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