3-Nitrobenzenesulfonyl chloride → 8-m-Nitrobenzenesulfonamido-1,3,6-naphthalenetrisulfonic acid

HRID 224338

Reaction equation

HRID 224338 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([S:20]([OH:23])(=[O:22])=[O:21])[CH:5]=[C:6]2[C:11]=1[C:10]([S:12]([OH:15])(=[O:14])=[O:13])=[CH:9][C:8]([S:16]([OH:19])(=[O:18])=[O:17])=[CH:7]2.C1C(N=NC2C(=O)N(C3C=CC(S([O-])(=O)=O)=CC=3)N=C2C([O-])=O)=CC=C(S([O-])(=O)=O)C=1.[Na+].[Na+].[Na+].C(=O)([O-])[O-].[Na+].[Na+].[N+:64]([C:67]1[CH:68]=[C:69]([S:73](Cl)(=[O:75])=[O:74])[CH:70]=[CH:71][CH:72]=1)([O-:66])=[O:65]>O>[N+:64]([C:67]1[CH:68]=[C:69]([S:73]([NH:1][C:2]2[CH:3]=[C:4]([S:20]([OH:23])(=[O:22])=[O:21])[CH:5]=[C:6]3[C:11]=2[C:10]([S:12]([OH:15])(=[O:14])=[O:13])=[CH:9][C:8]([S:16]([OH:19])(=[O:17])=[O:18])=[CH:7]3)(=[O:75])=[O:74])[CH:70]=[CH:71][CH:72]=1)([O-:66])=[O:65]

Participants

6

Reactant 4

HCID 84763-Nitrobenzenesulfonyl chloride2×HCID 10340Sodium Carbonate2×HCID 649518-Aminonaphthalene-1,3,6-trisulfonic acidHCID 164825Tartrazine

Product 1

HCID 131521328-m-Nitrobenzenesulfonamido-1,3,6-naphthalenetrisulfonic acidYield 80.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 21.9 g of 8-amino-1,3,6-naphthalenetrisulfonic acid, trisodium salt and 11.4 g of anhydrous sodium carbonate in 280 ml of water is added 24.0 g of m-nitrobenzenesulfonyl chloride. The mixture is stirred at room temperature for 16 hours, then an additional 1.0 g of sodium carbonate and 2.0 g of m-nitrobenzenesulfonyl chloride are added and stirring is continued for 3 hours longer. The mixture is evaporated and the residue is dissolved in 200 ml of water. A copious amount of absolute ethanol is added and the solid formed is collected and washed with ethanol and ether, then is dried to yield 26.1 g of 8-m-nitrobenzenesulfonamido-1,3,6-naphthalenetrisulfonic acid, trisodium salt.

Workup

  1. stirringstirring
  2. waitis continued for 3 hours
  3. customThe mixture is evaporated
  4. dissolutionthe residue is dissolved in 200 ml of water
  5. additionA copious amount of absolute ethanol is added
  6. customthe solid formed
  7. customis collected
  8. washwashed with ethanol and ether
  9. customis dried

Sources & evidence

ORD record
ord-9fce3d7684704acea5ef02fcfaa688f6
Source dataset
uspto-grants-1980_11
Patent number
US04231958

Linked notes

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