1,3,6-Naphthalenetrisulfonic acid, 8-amino-, sodium salt (1:?) → 8-(3-Nitro-2-sulfobenzamido)-1,3,6-naphthalene trisulfonic acid

HRID 66035

Reaction equation

HRID 66035 reaction equation
[Na+].[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(S(O)(=O)=O)=C(C=CC=1)C([O:43][C:44](=O)[C:45]1[CH:50]=[CH:49][CH:48]=[C:47]([N+:51]([O-:53])=[O:52])[C:46]=1[S:54]([OH:57])(=[O:56])=[O:55])=O)([O-])=O>O>[N+:51]([C:47]1[C:46]([S:54]([OH:57])(=[O:55])=[O:56])=[C:45]([CH:50]=[CH:49][CH:48]=1)[C:44]([NH:4][C:5]1[CH:6]=[C:7]([S:23]([OH:26])(=[O:25])=[O:24])[CH:8]=[C:9]2[C:14]=1[C:13]([S:15]([OH:18])(=[O:17])=[O:16])=[CH:12][C:11]([S:19]([OH:22])(=[O:20])=[O:21])=[CH:10]2)=[O:43])([O-:53])=[O:52]

Participants

5

Reactant 3

HCID 1018991,3,6-Naphthalenetrisulfonic acid, 8-amino-, sodium salt (1:?)HCID 151200803-Nitrosulfobenzoic anhydrideHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 542953508-(3-Nitro-2-sulfobenzamido)-1,3,6-naphthalene trisulfonic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A 6.6 g portion of 8-amino-1,3,6-naphthalenetrisulfonic acid trisodium salt and 2.92 g of sodium acetate trihydrate are dissolved in 180 ml of water at 2° C. A 4.0 g portion of 3-nitrosulfobenzoic anhydride is added with stirring. A 400 ml portion of water is added and the mixture is allowed to stand 21/2 hours, filtered and the filtrate is cooled, acidified with 2-3 ml of hydrochloric acid and diluted with ethanol. The pink solid is collected by filtration, washed with 85% ethanol, ether and dried giving 2.5 g of 8-(3-nitro-2-sulfobenzamido)-1,3,6-naphthalene trisulfonic acid, tetrasodium salt.

Workup

  1. custom2 hours
  2. filtrationfiltered
  3. temperaturethe filtrate is cooled
  4. additiondiluted with ethanol
  5. filtrationThe pink solid is collected by filtration
  6. washwashed with 85% ethanol, ether
  7. customdried

Sources & evidence

ORD record
ord-952bbe920ff443cdbdffbba7b9a69149
Source dataset
uspto-grants-1978_12
Patent number
US04129590

Linked notes

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