Tartrazine → 8-[5-(4-Nitro-2-sulfobenzamido)-o-toluenesulfonamido]-1,3,6-naphthalenetrisulfonic acid

HRID 263020Notes

Reaction equation

HRID 263020 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([S:9]([NH:12][C:13]2[CH:14]=[C:15]([S:31]([OH:34])(=[O:33])=[O:32])[CH:16]=[C:17]3[C:22]=2[C:21]([S:23]([OH:26])(=[O:25])=[O:24])=[CH:20][C:19]([S:27]([OH:30])(=[O:29])=[O:28])=[CH:18]3)(=[O:11])=[O:10])=[CH:4][CH:3]=1.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+].O.O.O.C([O-])(=O)C.[Na+].[N+](C1C=CC(C([O:86][C:87](=O)[C:88]2[CH:93]=[CH:92][C:91]([N+:94]([O-:96])=[O:95])=[CH:90][C:89]=2[S:97]([OH:100])(=[O:99])=[O:98])=O)=C(S(O)(=O)=O)C=1)([O-])=O>O>[N+:94]([C:91]1[CH:92]=[CH:93][C:88]([C:87]([NH:1][C:2]2[CH:7]=[C:6]([CH3:8])[C:5]([S:9]([NH:12][C:13]3[CH:14]=[C:15]([S:31]([OH:34])(=[O:33])=[O:32])[CH:16]=[C:17]4[C:22]=3[C:21]([S:23]([OH:26])(=[O:25])=[O:24])=[CH:20][C:19]([S:27]([OH:30])(=[O:28])=[O:29])=[CH:18]4)(=[O:11])=[O:10])=[CH:4][CH:3]=2)=[O:86])=[C:89]([S:97]([OH:100])(=[O:98])=[O:99])[CH:90]=1)([O-:96])=[O:95]

Participants

6

Reactant 4

HCID 164825TartrazineHCID 23665404Sodium Acetate TrihydrateHCID 570029234-Nitro-2-sulfobenzoic anhydrideHCID 867365468-(5-Amino-o-toluenesulfonamido)-1,3,6-naphthalenetrisulfonic acid

Product 1

HCID 867365458-[5-(4-Nitro-2-sulfobenzamido)-o-toluenesulfonamido]-1,3,6-naphthalenetrisulfonic acidYield 166.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 9.0 g of 8-(5-amino-o-toluenesulfonamido)-1,3,6-naphthalenetrisulfonic acid, trisodium salt, and 3.34 g of sodium acetate trihydrate in 47.0 ml of water chilled to 0° C. in an ice bath is added 4.29 g of 4-nitro-2-sulfobenzoic acid anhydride in one portion. The mixture is stirred for a total of 10 minutes in the ice bath and the undissolved material is separated. The solution, at 0° C., is acidified with 1.38 ml of concentrated hydrochloric acid, then is added dropwise, with vigorous stirring, to 750 ml of absolute ethanol. The product is collected, washed with 85% aqueous ethanol, ethanol and ether and is dried to yield 11.75 g of 8-[5-(4-nitro-2-sulfobenzamido)-o-toluenesulfonamido]-1,3,6-naphthalenetrisulfonic acid, tetrasodium salt.

Workup

  1. customthe undissolved material is separated
  2. customat 0° C.
  3. additionis added dropwise, with vigorous stirring, to 750 ml of absolute ethanol
  4. customThe product is collected
  5. washwashed with 85% aqueous ethanol, ethanol and ether
  6. customis dried

Sources & evidence

ORD record
ord-16fc354eefd946cbaeed50d77571b006
Source dataset
uspto-grants-1979_05
Patent number
US04155931

Reaction notes

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