Ethanol → Carfentrazone-ethyl

HRID 1851704Notes

Reaction equation

HRID 1851704 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].CC1C=CC(S(O)(=O)=O)=CC=1>CC1C=CC=CC=1C>[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 6101p-Toluenesulfonic acidHCID 443229Carfentrazone

Product 1

HCID 86222Carfentrazone-ethylYield 93%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

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 1, 140 g of ethanol, 1.9 g of 4-methylbenzenesulfonic acid and 400 g of dimethyl 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 sodium 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 93% with a purity of 99%. A HNMR spectrum of the carfentrazone-ethyl is showed in FIG. 1 and a mass spectrum thereof is showed in FIG. 2.

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 sodium hydroxide and finally with water
  6. customThe solvent was completely removed under reduced pressure

Sources & evidence

ORD record
ord-fecde4d16ff44fd4ae7f5e9234f9afd3
Source dataset
uspto-grants-2015_02
Patent number
US08957220B2

Reaction notes

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