Pyridine → 4-Benzoyloxy-3-(2-pyridylazo)-1-naphthalenesulfonic acid

HRID 1680385Notes

Reaction equation

HRID 1680385 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([S:12]([OH:15])(=[O:14])=[O:13])=[CH:4][C:3]=1[N:16]=[N:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1.N1C=CC=CC=1.[C:30](Cl)(=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(N(CC)CC)C>CC(C)=O>[C:30]([O:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([S:12]([OH:15])(=[O:13])=[O:14])=[CH:4][C:3]=1[N:16]=[N:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)(=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 827254-Hydroxy-3-[2-(2-pyridinyl)diazenyl]-1-naphthalenesulfonic acid

Product 1

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

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-Hydroxy-3-(2-pyridylazo)-1-naphthalenesulfonic acid (110 g) was added to pyridine (350 ml) followed by benzoyl chloride (250 ml). Triethylamine (100 ml) was added slowly and the reaction mixture got warm. After 1 hour the mixture was diluted with five times its volume of acetone and filtered. The product was washed with acetone and allowed to suck dry. It was dissolved in water (minimum volume) and neutralized with hydrochloric acid. After filtration, the product was washed with acetone and ether. Yield 120 g (83 percent).

Workup

  1. temperaturethe reaction mixture got warm
  2. filtrationfiltered
  3. washThe product was washed with acetone
  4. customto suck dry
  5. dissolutionIt was dissolved in water (minimum volume)
  6. filtrationAfter filtration
  7. washthe product was washed with acetone and ether

Sources & evidence

ORD record
ord-ef1742b914f44fe79399e34a94e04991
Source dataset
uspto-grants-1981_06
Patent number
US04273706

Reaction notes

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