Water → 1-Naphthalenesulfonyl chloride

HRID 2371361Notes

Reaction equation

HRID 2371361 reaction equation
[C:1]1([S:11]([O-:14])(=O)=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Na+].P(Cl)(Cl)([Cl:18])=O.O>C(#N)C.CC(N(C)C)=O>[C:1]1([S:11]([Cl:18])(=[O:14])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 23661867Sodium 1-naphthalenesulfonate

Product 1

HCID 665601-Naphthalenesulfonyl chloride

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
30 °C

Procedure

133 g of sodium α-naphthalenesulfonate was suspended in a mixture of 260 ml of acetonitrile and 7 ml of dimethylacetamide. 80 ml of phosphorus oxychloride was added dropwise to the suspension while being cooled with water at a temperature of lower than 50° C. After the dropwise addition was completed, the reaction system was further reacted at a temperature of 65° C. for 1 hour. After cooled to 30° C., the reaction mixture was poured into 2 l of ice water. The resulting grayish white crystal was filtered off, and air-dried. The yield was 110.8 g (84.6% of theoretical value). The melting point of the product was 66° to 68° C.

Workup

  1. additionAfter the dropwise addition
  2. customthe reaction system was further reacted at a temperature of 65° C. for 1 hour
  3. filtrationThe resulting grayish white crystal was filtered off
  4. customair-dried
  5. customwas 66° to 68° C.

Sources & evidence

ORD record
ord-0c9a896b58d041588bbf374f3bba6b46
Source dataset
uspto-grants-1992_03
Patent number
US05093229

Reaction notes

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