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

HRID 903848Notes

Reaction equation

HRID 903848 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-d5acaba2e5c243ccb55278117bfe1a69
Source dataset
uspto-grants-1980_10
Patent number
US04229370

Reaction notes

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