Sulfuric Acid → HCID 58088339, compound

HRID 249991Notes

Reaction equation

HRID 249991 reaction equation
COC1C=C(C[N:12]2[C:16](=[O:17])[C:15]([C:18]3[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=3)=[C:14]([CH3:28])[C:13]2=[O:29])C=CC=1OC.C(O)(C(F)(F)F)=O.OS(O)(=O)=O>C1(OC)C=CC=CC=1>[CH3:28][C:14]1[C:13](=[O:29])[NH:12][C:16](=[O:17])[C:15]=1[C:18]1[CH:19]=[CH:20][C:21]([C:24]([F:27])([F:25])[F:26])=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 6422Trifluoroacetic acidHCID 58088337HCID 58088337, compound

Product 1

HCID 58088339HCID 58088339, compoundYield 79.4%

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

A solution of 1-{[3,4-bis(methyloxy)phenyl]methyl}-3-methyl-4-[4-(trifluoromethyl)phenyl]-1H-pyrrole-2,5-dione (P3, 100 mg), anisole (107 μL), TFA (4 mL) and H2SO4 (catalytic amount) was heated at 90° C. overnight. The solution was then concentrated in vacuo, dichloromethane was added and the organic phase was washed with NaHCO3 (aqueous saturated solution), dried on sodium sulphate and evaporated in vacuo. The crude was purified by flash chromatography eluting with cyclohexane/ethyl acetate 8/2 to give the title compound (50 mg).

Workup

  1. concentrationThe solution was then concentrated in vacuo, dichloromethane
  2. additionwas added
  3. washthe organic phase was washed with NaHCO3 (aqueous saturated solution)
  4. customdried on sodium sulphate
  5. customevaporated in vacuo
  6. customThe crude was purified by flash chromatography
  7. washeluting with cyclohexane/ethyl acetate 8/2

Sources & evidence

ORD record
ord-910f334bf5c44a74b02762b237b00163
Source dataset
uspto-grants-2011_01
Patent number
US07863299B2

Reaction notes

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