Ethanol → Carfentrazone-ethyl

HRID 1851705Notes

Reaction equation

HRID 1851705 reaction equation
[Cl:1][CH:2]([CH2:6][C:7]1[CH:12]=[C:11]([N:13]2[C:17](=[O:18])[N:16]([CH:19]([F:21])[F:20])[C:15]([CH3:22])=[N:14]2)[C:10]([F:23])=[CH:9][C:8]=1[Cl:24])[C:3]([OH:5])=[O:4].[CH2:25](O)[CH3:26].S(=O)(=O)(O)O>CC1C=CC=CC=1>[CH3:25][CH2:26][O:4][C:3]([CH:2]([Cl:1])[CH2:6][C:7]1[CH:12]=[C:11]([N:13]2[N:14]=[C:15]([CH3:22])[N:16]([CH:19]([F:20])[F:21])[C:17]2=[O:18])[C:10]([F:23])=[CH:9][C:8]=1[Cl:24])=[O:5]

Participants

5

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 443229Carfentrazone

Product 1

HCID 86222Carfentrazone-ethylYield 92%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a flask was added 140 g of the 2-chloro-3-{2-chloro-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl]-4-fluorophenyl}propionic acid, obtained according to the Example 2, 160 g of ethanol, 7 g of sulfuric acid and 700 g of methyl benzene. The mixture was refluxed for 15 hours to remove water. The excess ethanol was recovered by distillation. At room temperature the mixture was washed with 200 g of water, with 200 g of a 4% (wt/wt) aqueous solution of potassium hydroxide and finally with water. The solvent was completely removed under reduced pressure to give carfentrazone-ethyl as a faint yellow transparent and viscous liquid in a yield of 92% with a purity of 98.8%.

Workup

  1. customobtained
  2. temperatureThe mixture was refluxed for 15 hours
  3. customto remove water
  4. distillationThe excess ethanol was recovered by distillation
  5. washAt room temperature the mixture was washed with 200 g of water, with 200 g of a 4% (wt/wt) aqueous solution of potassium hydroxide and finally with water
  6. customThe solvent was completely removed under reduced pressure

Sources & evidence

ORD record
ord-48a24c4e34a34d548de49560d66da678
Source dataset
uspto-grants-2015_02
Patent number
US08957220B2

Reaction notes

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