Thionyl Chloride → 6,7-Dimethoxynaphthalene-2-sulfonyl chloride

HRID 838960Notes

Reaction equation

HRID 838960 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH:9]=[C:8]([S:15]([O-:18])(=O)=[O:16])[CH:7]=[CH:6]2.[Na+].S(Cl)([Cl:22])=O>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH:9]=[C:8]([S:15]([Cl:22])(=[O:18])=[O:16])[CH:7]=[CH:6]2

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 23721231HCID 23721231, compound

Product 1

HCID 144577546,7-Dimethoxynaphthalene-2-sulfonyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred suspension of 50 g of finely divided sodium 6,7-dimethoxy-2-naphthalenesulfonate in 100 ml of dimethylformamide was added dropwise 62.2 ml of thionyl chloride at room temperature. After 30 minutes, the reaction mixture was poured into 1 l of ice water, and the precipitate filtered and then dissolved into 250 ml of benzene. The benzene solution was repeatedly washed with water and dried over anhydrous sodium sulfate. The solvent was evaporated to dryness in vacuo, and the residue was recrystallized from benzene-n-hexane (1:1) to give 32 g of 6,7-dimethoxy-2-naphthalenesulfonyl chloride, M.P. 127.5°-129.5° C

Workup

  1. filtrationthe precipitate filtered
  2. dissolutiondissolved into 250 ml of benzene
  3. washThe benzene solution was repeatedly washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated to dryness in vacuo
  6. customthe residue was recrystallized from benzene-n-hexane (1:1)

Sources & evidence

ORD record
ord-992af6f5bdf64d41ae96160798e8ee8f
Source dataset
uspto-grants-1978_06
Patent number
US04093712

Reaction notes

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