Tartrazine → 8-[3-(4-Nitro-2-sulfobenzamido)-p-toluamido]-1,3,5-naphthalenetrisulfonic acid

HRID 2052469Notes

Reaction equation

HRID 2052469 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH3:33])[CH:5]=[CH:6][C:7]=1[C:8]([NH:10][C:11]1[C:20]2[C:19]([S:21]([OH:24])(=[O:23])=[O:22])=[CH:18][C:17]([S:25]([OH:28])(=[O:27])=[O:26])=[CH:16][C:15]=2[C:14]([S:29]([OH:32])(=[O:31])=[O:30])=[CH:13][CH:12]=1)=[O:9].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:85][C:86](=O)[C:87]2[CH:92]=[CH:91][C:90]([N+:93]([O-:95])=[O:94])=[CH:89][C:88]=2[S:96]([OH:99])(=[O:98])=[O:97])=O)=C(S(O)(=O)=O)C=1)([O-])=O>O>[N+:93]([C:90]1[CH:91]=[CH:92][C:87]([C:86]([NH:1][C:2]2[CH:3]=[C:4]([CH3:33])[CH:5]=[CH:6][C:7]=2[C:8]([NH:10][C:11]2[C:20]3[C:19]([S:21]([OH:24])(=[O:23])=[O:22])=[CH:18][C:17]([S:25]([OH:28])(=[O:26])=[O:27])=[CH:16][C:15]=3[C:14]([S:29]([OH:32])(=[O:31])=[O:30])=[CH:13][CH:12]=2)=[O:9])=[O:85])=[C:88]([S:96]([OH:99])(=[O:97])=[O:98])[CH:89]=1)([O-:95])=[O:94]

Participants

6

Reactant 4

HCID 164825TartrazineHCID 23665404Sodium Acetate TrihydrateHCID 570029234-Nitro-2-sulfobenzoic anhydrideHCID 570945898(3-Amino-p-toluamido)-1,3,5-naphthalenetrisulfonic acid

Product 1

HCID 571629348-[3-(4-Nitro-2-sulfobenzamido)-p-toluamido]-1,3,5-naphthalenetrisulfonic acidYield 87.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 6.5 g of 8(3-amino-p-toluamido)-1,3,5-naphthalenetrisulfonic acid, trisodium salt (prepared in Example 1) and 2.4 g of sodium acetate trihydrate in 43.0 ml of water is added 3.07 g of 4-nitro-2-sulfobenzoic acid anhydride. The mixture is stirred for 30 minutes then is filtered. The filtrate is acidified with 0.98 ml of concentrated hydrochloric acid and evaporated in vacuo. The residue is dissolved in 20 ml of hot water which is added to 130 ml of absolute ethanol forming a gelatinous precipitate. The material is collected and washed with 80% aqueous ethanol, ethanol and ether and is dried to yield 4.2 g of 8-[3-(4-nitro-2-sulfobenzamido)-p-toluamido]-1,3,5-naphthalenetrisulfonic acid, tetrasodium salt.

Workup

  1. filtrationthen is filtered
  2. customevaporated in vacuo
  3. dissolutionThe residue is dissolved in 20 ml of hot water which
  4. additionis added to 130 ml of absolute ethanol forming a gelatinous precipitate
  5. customThe material is collected
  6. washwashed with 80% aqueous ethanol, ethanol and ether
  7. customis dried

Sources & evidence

ORD record
ord-a0859022a6804315b3fea7d064a0a53c
Source dataset
uspto-grants-1980_01
Patent number
US04185033

Reaction notes

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