Acetonitrile → 1-Naphthalenesulfonyl chloride

HRID 2165029Notes

Reaction equation

HRID 2165029 reaction equation
C(#N)C.CC(N(C)C)=O.[C:10]1([S:20]([O-:23])(=O)=[O:21])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1.[Na+].P(Cl)(Cl)([Cl:27])=O>O>[C:10]1([S:20]([Cl:27])(=[O:23])=[O:21])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 24813Phosphorus oxychlorideHCID 31374DimethylacetamideHCID 23661867Sodium 1-naphthalenesulfonate

Product 1

HCID 665601-Naphthalenesulfonyl chloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a mixed solution of 260 ml of acetonitrile and 7 ml of dimethylacetamide was suspended 133 g of sodium α-naphthalenesulfonate. While cooling the suspension with water, 80 ml of phosphorus oxychloride was dropwise added to the suspension. After the addition, the mixture was reacted at 65° C. for one hour. The reaction mixture was cooled and poured into 2 l of ice-cold water. The precipitated grayish-white crystals were recovered by filtration and air-dried. The yield was 110.8 g (84.6% of theoretical value), m.p. 66°-68° C.

Workup

  1. additionwas dropwise added to the suspension
  2. additionAfter the addition
  3. customthe mixture was reacted at 65° C. for one hour
  4. temperatureThe reaction mixture was cooled
  5. filtrationThe precipitated grayish-white crystals were recovered by filtration
  6. customair-dried

Sources & evidence

ORD record
ord-6dc51568e2ac48ae82b8e22779f2bd68
Source dataset
uspto-grants-1990_07
Patent number
US04939064

Reaction notes

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