HCID 23512963, compound → HCID 23512981, compound

HRID 354057Notes

Reaction equation

HRID 354057 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[OH:12][CH2:13][C:14]1[C:19]2[CH:20]=[CH:21][O:22][C:18]=2[C:17]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])=[CH:16][CH:15]=1>ClCCl>[CH:13]([C:14]1[C:19]2[CH:20]=[CH:21][O:22][C:18]=2[C:17]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])=[CH:16][CH:15]=1)=[O:12]

Participants

4

Reactant 2

HCID 23512963HCID 23512963, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 23512981HCID 23512981, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridinium chlorochromate (7.55 g, 35.0 mmole) was added into a solution of N-(4-hydroxymethyl-benzofuran-7-yl)-methanesulfonamide (5.69 g, 23.3 mmole) in dichloromethane (350 mL). The reaction mixture was stirred at room temperature for 16 hr and was partitioned between dichloromethane and water. The organic extract was dried (anhydrous sodium sulfate) and concentrated under reduced pressure. The residue was purified by flash column chromatography over silica gel eluting with 50% ethyl acetate in hexane to give N-(4-formyl-benzofuran-7-yl)-methanesulfonamide as solid (4.8 g, 86%). 1H NMR (DMSO-d6) δ: 3.26 (s, 3H), 7.48 (d, 1H, J=8.20 Hz), 7.51 (d, 1H, J=2.10 Hz), 7.88 (d, 1H, J=8.20 Hz), 8.29 (d, 1H, J=2.1 Hz), 10.12 (s, 1H), 10.63 (s, 1H). M−H: 238.

Workup

  1. customwas partitioned between dichloromethane and water
  2. extractionThe organic extract
  3. dry with materialwas dried (anhydrous sodium sulfate)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash column chromatography over silica gel eluting with 50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-7f477bc8c7014bf08af7f52ba03b8918
Source dataset
uspto-grants-2004_06
Patent number
US06756395B2

Reaction notes

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