Thionyl Chloride → 4-Benzoyloxy-3-(2-pyridylazo)-1-naphthalenesulfonyl chloride

HRID 1680384Notes

Reaction equation

HRID 1680384 reaction equation
[C:1]([O:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([S:20](O)(=[O:22])=[O:21])=[CH:12][C:11]=1[N:24]=[N:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:34])=O>CN(C)C=O>[C:1]([O:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([S:20]([Cl:34])(=[O:22])=[O:21])=[CH:12][C:11]=1[N:24]=[N:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 234561594-Benzoyloxy-3-(2-pyridylazo)-1-naphthalenesulfonic acid

Product 1

HCID 234561604-Benzoyloxy-3-(2-pyridylazo)-1-naphthalenesulfonyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Benzoyloxy-3-(2-pyridylazo)-1-naphthalenesulfonic acid (70 g) was added to thionyl chloride (300 ml). Dimethylformamide (30 ml) was added in portions while the reaction mixture was being stirred. After 1 hour the starting material was all in solution. The reaction mixture was poured into a large quantity of ice after a further 4 hours' stirring. The product was filtered off and dissolved in chloroform. The chloroform layer was shaken with water to destroy any remaining thionyl chloride and dried over magnesium sulfate.

Workup

  1. additionThe reaction mixture was poured into a large quantity of ice after a further 4 hours'
  2. stirringstirring
  3. filtrationThe product was filtered off
  4. dissolutiondissolved in chloroform
  5. stirringThe chloroform layer was shaken with water
  6. customto destroy any remaining thionyl chloride
  7. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-aea4bbe39c694b5bb462fd1092a8af76
Source dataset
uspto-grants-1981_06
Patent number
US04273706

Reaction notes

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