Phosphorus oxychloride → 2-Naphthalenesulfonyl chloride, 5-(acetylamino)-1-(acetyloxy)-

HRID 1579950Notes

Reaction equation

HRID 1579950 reaction equation
[C:1]([NH:4][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH:7]=[CH:8][C:9]([S:19]([O-:22])(=O)=[O:20])=[C:10]2[O:15][C:16](=[O:18])[CH3:17])(=[O:3])[CH3:2].[Na+].P(Cl)(Cl)([Cl:26])=O>CN(C)C=O>[C:1]([NH:4][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH:7]=[CH:8][C:9]([S:19]([Cl:26])(=[O:22])=[O:20])=[C:10]2[O:15][C:16](=[O:18])[CH3:17])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 236637052-Naphthalenesulfonic acid, 5-(acetylamino)-1-(acetyloxy)-, sodium salt (1:1)

Product 1

HCID 941252-Naphthalenesulfonyl chloride, 5-(acetylamino)-1-(acetyloxy)-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The 5-acetamido-1-acetoxynaphthalene-2-sulfonyl chloride was prepared by dropwise treatment of a suspension of dry sodium 5-acetamido-1-acetoxynaphthalene-2-sulfonate in 100 ml. phosphoryl chloride with 5.5 ml. dry dimethylformamide in a nitrogen atmosphere. The reaction mixture was stirred 1 hour and then poured over 600 ml. of crushed ice. The crude product was filtered and dissolved immediately in 500 ml. chloroform. The solution was treated with activated charcoal and dried over anhydrous magnesium sulfate to give 10.8 g. (44%) of a resinous yellow product which showed a single spot on a thin-layer chromotography.

Workup

  1. additionpoured over 600 ml
  2. filtrationThe crude product was filtered
  3. dissolutiondissolved immediately in 500 ml
  4. additionThe solution was treated with activated charcoal
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customto give 10.8 g

Sources & evidence

ORD record
ord-8bdaf14dda4e414daee19a6d707207f1
Source dataset
uspto-grants-1976_01
Patent number
US03932380

Reaction notes

Loading…