Methanol → HCID 57325920, compound

HRID 507944Notes

Reaction equation

HRID 507944 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH:13][C:14]1[CH:26]=[CH:25][C:17]2[C:18]([CH2:21][C:22]([OH:24])=[O:23])=[CH:19][O:20][C:16]=2[CH:15]=1)(=[O:12])=[O:11])([O-:3])=[O:2].S(Cl)(Cl)=O.[CH3:31]O>>[CH3:31][O:23][C:22](=[O:24])[CH2:21][C:18]1[C:17]2[CH:25]=[CH:26][C:14]([NH:13][S:10]([C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N+:1]([O-:3])=[O:2])(=[O:11])=[O:12])=[CH:15][C:16]=2[O:20][CH:19]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 23157318HCID 23157318, compound

Product 1

HCID 57325920HCID 57325920, compoundYield 62%

Procedure

(6-{[(2-Nitrophenyl)sulfonyl]amino}-1-benzofuran-3-yl)acetic acid (2.84 g, 7.55 mmol) was suspended in methanol (8 mL), and thionyl chloride (2 mL, 27.4 mmol) was added dropwise under ice-cooling. After completion of the dropwise addition, the mixture was stirred at room temperature for 2.5 hr. The reaction mixture was concentrated under reduced pressure. Water was added and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (20%-60% ethyl acetate/hexane), and the obtained solid was recrystallized from ethyl acetate-hexane to give the title compound (1.82 g, yield 62%) as yellow prism crystals.

Workup

  1. temperaturecooling
  2. additionAfter completion of the dropwise addition
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionWater was added
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe extract was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (20%-60% ethyl acetate/hexane)
  10. customthe obtained solid was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-dbd51d72d6164c4b9f2c8fe808114de3
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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