HCID 23512963, compound → HCID 23512981, compound

HRID 2217372Notes

Reaction equation

HRID 2217372 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-886589b49e434a07957f130b73b7b4bb
Source dataset
uspto-grants-2008_08
Patent number
US07407980B2

Reaction notes

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