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

HRID 2198548

Reaction equation

HRID 2198548 reaction equation
[C:1]([O:4][C:5]1[C:14]2[C:9](=[C:10]([NH:15][C:16]([CH3:18])=[O:17])[CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][C:6]=1[S:19]([OH:22])(=O)=[O:20])(=[O:3])[CH3:2].S1(CCCC1)(=O)=O.P(Cl)(Cl)([Cl:32])=O>>[C:1]([O:4][C:5]1[C:14]2[C:9](=[C:10]([NH:15][C:16]([CH3:18])=[O:17])[CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][C:6]=1[S:19]([Cl:32])(=[O:22])=[O:20])(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 31347SulfolaneHCID 1556985-Acetamido-1-(acetyloxy)naphthalene-2-sulfonic acid

Product 1

HCID 941252-Naphthalenesulfonyl chloride, 5-(acetylamino)-1-(acetyloxy)-Yield 81%

Conditions

Temperature
40 °C

Procedure

100 g of 1-acetoxy-5-acetaminonaphthalene-2-sulfonic acid was added to 500 ml of sulfolane, and 200 ml of phosphorus oxychloride was dropwise added thereto at 40° C. while stirring. After continuing stirring for about 1 hour, the reaction mixture was poured into 2 liters of ice-water, and the precipitated crystals were collected by filtration, washed with water until the filtrate did not show acidity, and air-dried as such for 24 hours to obtain 70 g (81% yield) of product.

Workup

  1. additionwas dropwise added
  2. stirringAfter continuing stirring for about 1 hour
  3. filtrationthe precipitated crystals were collected by filtration
  4. washwashed with water until the filtrate
  5. customair-dried as such for 24 hours

Sources & evidence

ORD record
ord-b241a5edfd5e451ebbba5e3298b4e286
Source dataset
uspto-grants-1982_11
Patent number
US04358532

Linked notes

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