Water → 6-methoxynaphthalene-2-sulfonyl Chloride

HRID 1694284Notes

Reaction equation

HRID 1694284 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[C:12]([S:17]([O-:20])(=O)=[O:18])[CH:11]=[CH:10]2.O>CN(C=O)C>[CH3:5][O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[C:12]([S:17]([Cl:3])(=[O:20])=[O:18])[CH:11]=[CH:10]2

Participants

5

Reactant 3

HCID 962WaterHCID 24386Thionyl ChlorideHCID 4337104HCID 4337104, compound

Product 1

HCID 106348626-methoxynaphthalene-2-sulfonyl Chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydroxide (0.7 g) was added to a solution of sodium 6-hydroxynapthalene-2-sulfonate (9 mmol) in water (20 ml). Dimethyl sulfate (1.1 eq.) was added to this solution at 50-55° C. over 1 h, followed by sodium chloride (3.3 g). The solid that was formed was filtered off, washed with saturated NaCl solution and toluene and dried. Yield: 75% 2. Thionyl chloride (0.25 ml) was added to a cooled solution of 6-methoxynaphthalene-2-sulfonate (2 mmol) in dry DMF (1 ml) under N2. The reaction mixture was stirred for 3 h at 0° C. Iced water (20 ml) was added to the mixture, the solid was filtered off and washed with iced water. The solid was taken up in DCM (25 ml), the solution dried over Na2SO4, filtered and concentrated under reduced pressure. Yield: 75%

Workup

  1. filtrationthe solid was filtered off
  2. washwashed with iced water
  3. dry with materialthe solution dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-33530d3a91884011ae312fb57fe70b79
Source dataset
uspto-grants-2012_04
Patent number
US08158628B2

Reaction notes

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