Potassium Hydroxide → Clomazone

HRID 260261

Reaction equation

HRID 260261 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

One method for production of COMMAND® is disclosed in U.S. Pat. No. 4,405,357. Such preparation includes adding to a stirred solution of 6.3 grams (0.023 mole) of 3-chloro-N-(2-chlorophenyl)methyl-N-hydroxy-2,2-dimethylpropanamide in 45 ml of methanol dropwise a solution of 1.5 grams (0.023 mole) KOH (85% pure) in 25 ml methanol. The addition required 15 minutes and the temperature rose from 24 to 32° C. Upon completion of addition the reaction mixture was stirred for 18 hours at ambient temperature. By-product KCl was removed by filtering the mixture. 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 MgSO4 and filtered. Under reduced pressure the filtrate was concentrated to give 5.2 grams of 2-(2-chlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone as an oil.

Workup

  1. customSuch preparation
  2. additionThe addition required 15 minutes
  3. customrose from 24 to 32° C
  4. additionUpon completion of addition the reaction mixture
  5. customBy-product KCl was removed
  6. filtrationby filtering the mixture
  7. additionThe filtrate was poured into 500 ml of ice-water
  8. extractionThe mixture was extracted with two portions of 250 ml each of methylene chloride
  9. dry with materialThe combined extracts were dried with MgSO4
  10. filtrationfiltered
  11. concentrationUnder reduced pressure the filtrate was concentrated

Sources & evidence

ORD record
ord-819453be51544e1dbe0a367d84dcb21e
Source dataset
uspto-grants-1996_06
Patent number
US05527762

Linked notes

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