Water → HCID 86620744, compound

HRID 554301Notes

Reaction equation

HRID 554301 reaction equation
[C:1]1([C:7]2[N:11]([S:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[CH:10]=[C:9]([CH:25]=[O:26])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:27]N1C(=O)CCC1=O.O>CN(C)C=O>[Cl:27][C:10]1[N:11]([S:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:22])[F:23])=[CH:17][CH:16]=2)(=[O:13])=[O:14])[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:8][C:9]=1[CH:25]=[O:26]

Participants

5

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 86620737HCID 86620737, compound

Product 1

HCID 86620744HCID 86620744, compoundYield 61.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Phenyl-1-{[4-(trifluoromethyl)phenyl]sulfonyl}-1H-pyrrole-3-carbaldehyde (300 mg) was dissolved in N,N-dimethylformamide (6 mL), N-chlorosuccinimide (116 mg) was added at room temperature, and the mixture was stirred for 24 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with 3% potassium hydrogensulfate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=19:1→4:1) to give the title compound as colorless crystals (yield 200 mg, 61%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with 3% potassium hydrogensulfate solution and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=19:1→4:1)

Sources & evidence

ORD record
ord-323a41cccb5a4a77ba3f16654650fd6e
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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