1,3,6-Naphthalenetrisulfonic acid, 8-amino-, sodium salt (1:?) → 8-(4-Nitro-2-sulfobenzamido)-1,3,6-naphthalenetrisulfonic acid tetrasodium salt

HRID 1447570

Reaction equation

HRID 1447570 reaction equation
[Na+:1].[Na+].[Na+].[NH2:4][C:5]1[CH:6]=[C:7]([S:23]([O-:26])(=[O:25])=[O:24])[CH:8]=[C:9]2[C:14]=1[C:13]([S:15]([O-:18])(=[O:17])=[O:16])=[CH:12][C:11]([S:19]([O-:22])(=[O:21])=[O:20])=[CH:10]2.O.O.O.C([O-])(=O)C.[Na+].[N+](C1C=CC(C([O:44][C:45](=O)[C:46]2[CH:51]=[CH:50][C:49]([N+:52]([O-:54])=[O:53])=[CH:48][C:47]=2[S:55]([OH:58])(=[O:57])=[O:56])=O)=C(S(O)(=O)=O)C=1)([O-])=O>O>[Na+:1].[Na+:1].[Na+:1].[Na+:1].[N+:52]([C:49]1[CH:50]=[CH:51][C:46]([C:45]([NH:4][C:5]2[CH:6]=[C:7]([S:23]([O-:26])(=[O:25])=[O:24])[CH:8]=[C:9]3[C:14]=2[C:13]([S:15]([O-:18])(=[O:17])=[O:16])=[CH:12][C:11]([S:19]([O-:22])(=[O:20])=[O:21])=[CH:10]3)=[O:44])=[C:47]([S:55]([OH:58])(=[O:56])=[O:57])[CH:48]=1)([O-:54])=[O:53]

Participants

5

Reactant 3

HCID 1018991,3,6-Naphthalenetrisulfonic acid, 8-amino-, sodium salt (1:?)HCID 23665404Sodium Acetate TrihydrateHCID 570029234-Nitro-2-sulfobenzoic anhydride

Product 1

HCID 1317113688-(4-Nitro-2-sulfobenzamido)-1,3,6-naphthalenetrisulfonic acid tetrasodium salt

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an ice-bath cooled solution (5° C.) of 8-amino-1,3,6-naphthalenetrisulfonic acid trisodium salt and 6.7 g of sodium acetate trihydrate in 100 ml of water is added 8.8 g of 4-nitro-2-sulfobenzoic acid anhydride. The mixture is stirred vigorously for 10 minutes and is filtered. The filtrate is cooled in an ice bath and diluted with 500 ml of cold ethyl alcohol. The mixture is filtered and the product is washed with ethyl alcohol and ether and then is dried. The product is dissolved in 50 ml of warm water and is stirred for 10 minutes after the addition of one ml of acetone. The mixture is treated with activated charcoal, filtered through diatomaceous earth and is washed with 20 ml of water. The filtrate is cooled in an ice bath and acidified with 1.5 ml of concentrated hydrochloric acid. The solution is diluted with 500 ml of cold ethyl alcohol, and the precipitated material is filtered, washed with ethanol followed by ether and dried. The above purification process is repeated without acidification. The product obtained is dried overnight at 110° C. to give 18.5 g of 8-(4-nitro-2-sulfobenzamido)-1,3,6-naphthalenetrisulfonic acid tetrasodium salt.

Workup

  1. filtrationis filtered
  2. temperatureThe filtrate is cooled in an ice bath
  3. additiondiluted with 500 ml of cold ethyl alcohol
  4. filtrationThe mixture is filtered
  5. washthe product is washed with ethyl alcohol and ether
  6. customis dried
  7. dissolutionThe product is dissolved in 50 ml of warm water
  8. stirringis stirred for 10 minutes
  9. additionafter the addition of one ml of acetone
  10. additionThe mixture is treated with activated charcoal
  11. filtrationfiltered through diatomaceous earth
  12. washis washed with 20 ml of water
  13. temperatureThe filtrate is cooled in an ice bath
  14. additionThe solution is diluted with 500 ml of cold ethyl alcohol
  15. filtrationthe precipitated material is filtered
  16. washwashed with ethanol
  17. customdried
  18. customThe above purification process
  19. customThe product obtained
  20. customis dried overnight at 110° C.

Sources & evidence

ORD record
ord-97f8776749c74c99978ac63f8e98c66a
Source dataset
uspto-grants-1979_12
Patent number
US04177209

Linked notes

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