Potassium Hydroxide → 5-Chloro-2-[(2-chlorophenyl)methyl]-4,4-dimethyl-1,2-oxazolidin-3-one

HRID 1995485Notes

Reaction equation

HRID 1995485 reaction equation
[Cl:1][CH:2](Cl)[C:3]([CH3:17])([CH3:16])[C:4]([N:6]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[Cl:15])[OH:7])=[O:5].[OH-].[K+]>CO.CCCCCC.CCCCCCC>[Cl:1][CH:2]1[O:7][N:6]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[Cl:15])[C:4](=[O:5])[C:3]1([CH3:17])[CH3:16]

Participants

6

Reactant 2

HCID 14797Potassium HydroxideHCID 13192550HCID 13192550, compound

Product 1

HCID 131925865-Chloro-2-[(2-chlorophenyl)methyl]-4,4-dimethyl-1,2-oxazolidin-3-oneYield 24.8%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8058HexaneSolventHCID 8900HeptaneSolvent

Procedure

These compounds were prepared in the manner of Example 16, using 7.7 grams (0.025 mole) of 3,3-dichloro-N-(2-chlorophenyl)methyl-N-hydroxy-2,2-dimethylpropanamide (prepared in Example 10) and 1.6 grams (0.025 mole) of 85% pure potassium hydroxide in 70 ml of methanol. Thin layer chromatographic analysis of the reaction mixture on silica gel using 20% ethyl acetate in hexane as an eluent indicated that the reaction mixture was a two-component mixture. The crude reaction mixture was subjected to column chromatography on silica gel using 15% ethyl acetate in heptane. Initial fractions from the chromatography were combined to give 1.7 grams of 5-chloro-2-(2-chlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone as an oil.

Workup

  1. customThese compounds were prepared in the manner of Example 16
  2. customThe crude reaction mixture

Sources & evidence

ORD record
ord-5f0507c449504371b3cb71c122796a91
Source dataset
uspto-grants-1983_09
Patent number
US04405357

Reaction notes

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