Iodine → HCID 117601618, compound

HRID 1773755Notes

Reaction equation

HRID 1773755 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH:13]=[CH:12][C:10]([NH2:11])=[C:9]([N+:14]([O-:16])=[O:15])[CH:8]=2)=[C:5]([CH3:17])[O:4][N:3]=1.[I:18]I>C(O)C.[N+]([O-])([O-])=O.[Ag+]>[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9]([N+:14]([O-:16])=[O:15])[C:10]([NH2:11])=[C:12]([I:18])[CH:13]=2)=[C:5]([CH3:17])[O:4][N:3]=1

Participants

5

Reactant 2

HCID 807IodineHCID 117601838HCID 117601838, compound

Product 1

HCID 117601618HCID 117601618, compoundYield 76.5%

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 702EthanolSolvent

Procedure

To a solution of compound 4-(3,5-dimethylisoxazol-4-yl)-2-nitroaniline (334 g, 1.43 mol, 1.0 eq) in ethanol (3.3 L) were added iodine (726 g, 2.8 mol, 2.0 eq) and silver nitrate (485 g, 2.8 mol, 2.0 eq). The reaction mixture was stirred at rt overnight, filtered, and the filtrate was evaporated to dryness. The residue was dissolved in EtOAc (5 L) and washed with water and brine, and dried over sodium sulfate. The organic solvent was evaporated to give a residue, which was purified by flash column chromatography on silica gel (PE/EA=4:1-3:1) to give compound 393 g of 4-(3,5-dimethylisoxazol-4-yl)-2-iodo-6-nitroaniline as an orange solid.

Workup

  1. filtrationfiltered
  2. customthe filtrate was evaporated to dryness
  3. dissolutionThe residue was dissolved in EtOAc (5 L)
  4. washwashed with water and brine
  5. dry with materialdried over sodium sulfate
  6. customThe organic solvent was evaporated
  7. customto give a residue, which
  8. customwas purified by flash column chromatography on silica gel (PE/EA=4:1-3:1)

Sources & evidence

ORD record
ord-014206bd8c854835bc6dcd280b6a0213
Source dataset
uspto-grants-2016_02
Patent number
US09255089B2

Reaction notes

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