Potassium Hydroxide → Clomazone

HRID 1995484Notes

Reaction equation

HRID 1995484 reaction equation
Cl[CH2:2][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>[Cl:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[CH2:8][N:6]1[C:4](=[O:5])[C:3]([CH3:17])([CH3:16])[CH2:2][O:7]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 99255583-chloro-N-(2-chlorophenyl)methyl-N-hydroxy-2,2-dimethylpropanamide

Product 1

HCID 54778ClomazoneYield 94.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a stirred solution of 6.3 grams (0.023 mole) of 3-chloro-N-(2-chlorophenyl)methyl-N-hydroxy-2,2-dimethylpropanamide (prepared in Example 1) in 45 ml of methanol was added dropwise a solution of 1.5 grams (0.023 mole) potassium hydroxide (85% pure) in 25 ml of methanol. The addition required 15 minutes during which time the reaction mixture temperature rose from 24° to 32°. Upon completion of addition the reaction mixture was stirred for 18 hours at ambient temperature. The reaction mixture was filtered to remove by-product potassium chloride. The filtrate was poured into 500 ml of ice-water. The mixture was extracted with two portions of 250 ml each of methylene chloride. The combined extracts were dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to give 5.2 grams of 2-(2-chlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone as an oil.

Workup

  1. additionThe addition required 15 minutes during which time the reaction mixture temperature
  2. customrose from 24° to 32°
  3. additionUpon completion of addition the reaction mixture
  4. filtrationThe reaction mixture was filtered
  5. customto remove by-product potassium chloride
  6. additionThe filtrate was poured into 500 ml of ice-water
  7. extractionThe mixture was extracted with two portions of 250 ml each of methylene chloride
  8. dry with materialThe combined extracts were dried with magnesium sulfate
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-94ce890ed03b4f9ea01e933188cfb8f6
Source dataset
uspto-grants-1983_09
Patent number
US04405357

Reaction notes

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