3-Nitrobenzenesulfonyl chloride → 8-(3-m-Nitrobenzenesulfonamido-p-toluenesulfonamido)-1,3,5-naphthalenetrisulfonic acid

HRID 903847Notes

Reaction equation

HRID 903847 reaction equation
[Na+].[Na+].[Na+].[NH2:4][C:5]1[CH:6]=[C:7]([CH3:37])[CH:8]=[CH:9][C:10]=1[S:11]([NH:14][C:15]1[C:24]2[C:23]([S:25]([O-:28])(=[O:27])=[O:26])=[CH:22][C:21]([S:29]([O-:32])(=[O:31])=[O:30])=[CH:20][C:19]=2[C:18]([S:33]([O-:36])(=[O:35])=[O:34])=[CH:17][CH:16]=1)(=[O:13])=[O:12].C(=O)([O-])[O-].[Na+].[Na+].[N+:44]([C:47]1[CH:48]=[C:49]([S:53](Cl)(=[O:55])=[O:54])[CH:50]=[CH:51][CH:52]=1)([O-:46])=[O:45]>O>[N+:44]([C:47]1[CH:48]=[C:49]([S:53]([NH:4][C:5]2[CH:6]=[C:7]([CH3:37])[CH:8]=[CH:9][C:10]=2[S:11]([NH:14][C:15]2[C:24]3[C:23]([S:25]([OH:28])(=[O:27])=[O:26])=[CH:22][C:21]([S:29]([OH:32])(=[O:30])=[O:31])=[CH:20][C:19]=3[C:18]([S:33]([OH:36])(=[O:35])=[O:34])=[CH:17][CH:16]=2)(=[O:13])=[O:12])(=[O:55])=[O:54])[CH:50]=[CH:51][CH:52]=1)([O-:46])=[O:45]

Participants

5

Reactant 3

HCID 84763-Nitrobenzenesulfonyl chloride2×HCID 10340Sodium Carbonate2×HCID 1317115108-(3-Amino-p-toluenesulfonamido)-1,3,5-naphthalenetrisulfonic acid trisodium salt

Product 1

HCID 867365508-(3-m-Nitrobenzenesulfonamido-p-toluenesulfonamido)-1,3,5-naphthalenetrisulfonic acidYield 29.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 2.0 g of 8-(3-amino-p-toluenesulfonamido)-1,3,5-naphthalenetrisulfonic acid trisodium salt and 342 mg of anhydrous sodium carbonate in 10 ml of water is added 1.5 g of m-nitrobenzenesulfonyl chloride. The mixture is stirred for 16 hours. An additional 170 mg of anhydrous sodium carbonate is added followed by 750 mg of m-nitrobenzenesulfonyl chloride and the mixture is stirred for an additional 16 hours. The reaction mixture is evaporated and the residue dissolved in hot water. A product is precipitated on the addition of absolute ethanol. The product is collected, washed with ethanol and ether and dried. Additional product is collected from the filtrate and is washed and dried as above. The above fractions of product are combined and dissolved in water, then 2.5 ml of 5 N sodium hydroxide is added and the mixture is stirred for 30 minutes. The mixture is acidified with glacial acetic acid and evaporated. The residue is dissolved in hot water and precipitated with ethanol. The product is collected and washed twice with ethanol and ether and dried to yield 700 mg of 8-(3-m-nitrobenzenesulfonamido-p-toluenesulfonamido)-1,3,5-naphthalenetrisulfonic acid, trisodium salt.

Workup

  1. stirringthe mixture is stirred for an additional 16 hours
  2. customThe reaction mixture is evaporated
  3. dissolutionthe residue dissolved in hot water
  4. customA product is precipitated on the addition of absolute ethanol
  5. customThe product is collected
  6. washwashed with ethanol and ether
  7. customdried
  8. customAdditional product is collected from the filtrate
  9. washis washed
  10. customdried as above
  11. dissolutiondissolved in water
  12. addition2.5 ml of 5 N sodium hydroxide is added
  13. stirringthe mixture is stirred for 30 minutes
  14. customevaporated
  15. dissolutionThe residue is dissolved in hot water
  16. customprecipitated with ethanol
  17. customThe product is collected
  18. washwashed twice with ethanol and ether
  19. customdried

Sources & evidence

ORD record
ord-3a626c75b2534fd0a01c63705aae2b86
Source dataset
uspto-grants-1980_10
Patent number
US04229370

Reaction notes

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