HCID 19880767, compound → HCID 57231206, compound

HRID 847335Notes

Reaction equation

HRID 847335 reaction equation
[Cl:1][C:2]1[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[C:20]([F:28])[C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([N+:17]([O-])=O)=[C:9]([S:11][CH:12]([CH3:16])[C:13](O)=[O:14])[CH:10]=1>C(O)(=O)C>[Cl:1][C:2]1[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[C:20]([F:28])[C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]2[NH:17][C:13](=[O:14])[CH:12]([CH3:16])[S:11][C:9]=2[CH:10]=1

Participants

3

Reactant 1

HCID 19880767HCID 19880767, compound

Product 1

HCID 57231206HCID 57231206, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

Reduced iron (1.3 g) was suspended in acetic acid (6 ml), a solution of 2-[5-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-2-nitrophenylthio]propionic acid (1.5 g) in acetic acid (2 ml) was added to the suspension, and the mixture was vigorously stirred for 20 hr. After the completion of the reaction, the reaction mixture was filtered and concentrated in vacuo, and the residue was extracted with ethyl acetate (50 ml×2), washed with water and a saturated saline solution and dried over anhydrous magnesium sulfate. The solvent was distilled off in vacuo, and the residue was purified by silica gel column chromatography (developing solvent: n-hexane/ethyl acetate=3/1) to prepare the title compound (0.9 g) as a colorless crystal (yield: 69%).

Workup

  1. customAfter the completion of the reaction
  2. filtrationthe reaction mixture was filtered
  3. concentrationconcentrated in vacuo
  4. extractionthe residue was extracted with ethyl acetate (50 ml×2)
  5. washwashed with water
  6. dry with materiala saturated saline solution and dried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off in vacuo
  8. customthe residue was purified by silica gel column chromatography (developing solvent: n-hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-b597b4fcbd814a9fa65b02a7334ff526
Source dataset
uspto-grants-1992_08
Patent number
US05141551

Reaction notes

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