Thionyl Chloride → 7-methoxynaphthalene-2-sulfonyl Chloride

HRID 619838Notes

Reaction equation

HRID 619838 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([S:13]([OH:16])(=O)=[O:14])=[CH:10]2)=[CH:5][CH:4]=1.[Na].S(Cl)([Cl:20])=O>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([S:13]([Cl:20])(=[O:16])=[O:14])=[CH:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 5360545SodiumHCID 22665846HCID 22665846, compound

Product 1

HCID 105152667-methoxynaphthalene-2-sulfonyl Chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Conditions

Temperature
80 °C

Procedure

A mixture of 7-methoxynaphthalene-2-sulfonic acid, sodium salt (8.12 g, 31.1 mmol) in 80 mL of thionyl chloride is heated at 80° C. for 3 hours. A few drops of DMF is added with vigorous bubbling resulting and the mixture is heated for an additional 1.5 hours. The mixture is allowed to cool to room temperature and concentrated in vacuo. The residue is diluted in EtOAc and washed successively with water (2×), 1 N HCl solution and saturated NaCl. The organic layer is dried over anhydrous MgSO4, filtered and concentrated. The crude product is purified by column chromatography eluting with 20% EtOAc/hexanes to afford the title compound (5.2 g, 20.2 mmol) as a white solid.

Workup

  1. customwith vigorous bubbling
  2. customresulting
  3. temperaturethe mixture is heated for an additional 1.5 hours
  4. temperatureto cool to room temperature
  5. concentrationconcentrated in vacuo
  6. additionThe residue is diluted in EtOAc
  7. washwashed successively with water (2×), 1 N HCl solution and saturated NaCl
  8. dry with materialThe organic layer is dried over anhydrous MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe crude product is purified by column chromatography
  12. washeluting with 20% EtOAc/hexanes

Sources & evidence

ORD record
ord-03bb5229b3e447c6b49f3126a3ab7462
Source dataset
uspto-grants-1999_09
Patent number
US05958918

Reaction notes

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