5-Nitroisophthaloyl chloride → 2'-Methyl-5-nitro-5'-(4,6,8-trisulfo-1-naphthylcarbamoyl)isophthalanilic acid

HRID 2052468Notes

Reaction equation

HRID 2052468 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:13](Cl)=[O:14])[CH:7]=C([CH:12]=1)C(Cl)=O)([O-:3])=[O:2].N[C:17]1[CH:18]=[C:19]([CH3:48])[CH:20]=[CH:21][C:22]=1[C:23]([NH:25][C:26]1[C:35]2[C:34]([S:36]([OH:39])(=[O:38])=[O:37])=[CH:33][C:32]([S:40]([OH:43])(=[O:42])=[O:41])=[CH:31][C:30]=2[C:29]([S:44]([OH:47])(=[O:46])=[O:45])=[CH:28][CH:27]=1)=[O:24].C1C([N:55]=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:86]([O-:89])(=[O:88])[CH3:87].[Na+]>CCOCC.O>[CH3:48][C:19]1[CH:18]=[CH:17][C:22]([C:23](=[O:24])[NH:25][C:26]2[C:35]3[C:30](=[CH:31][C:32]([S:40]([OH:43])(=[O:42])=[O:41])=[CH:33][C:34]=3[S:36]([OH:39])(=[O:37])=[O:38])[C:29]([S:44]([OH:47])(=[O:45])=[O:46])=[CH:28][CH:27]=2)=[CH:21][C:20]=1[NH:55][C:13](=[O:14])[C:6]1[CH:7]=[C:87]([CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)[C:86]([OH:89])=[O:88]

Participants

7

Reactant 4

HCID 834515-Nitroisophthaloyl chlorideHCID 164825TartrazineHCID 23665404Sodium Acetate TrihydrateHCID 570945898(3-Amino-p-toluamido)-1,3,5-naphthalenetrisulfonic acid

Product 1

HCID 203767912'-Methyl-5-nitro-5'-(4,6,8-trisulfo-1-naphthylcarbamoyl)isophthalanilic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 2.78 g of 5-nitroisophthaloyl chloride in 50 ml of ether is added to a stirred mixture of 6.5 g of 8-(3-amino-p-toluamido)-1,3,5-naphthalenetrisulfonic acid, trisodium salt, 3.2 g of sodium acetate trihydrate, 50 ml of water and 40 ml of ether over a 40 minute period. The mixture is stirred for an additional 30 minutes, then is evaporated. The residue is dissolved in 20 ml of hot water, then is placed in an icebox overnight. The precipitate is collected, washed with ice-water, 80% aqueous ethanol, ethanol and ether and is dried to yield 2.9 g of 2'-methyl-5-nitro-5'-(4,6,8-trisulfo-1-naphthylcarbamoyl)isophthalanilic acid, trisodium salt.

Workup

  1. customis evaporated
  2. dissolutionThe residue is dissolved in 20 ml of hot water
  3. waitis placed in an icebox overnight
  4. customThe precipitate is collected
  5. washwashed with ice-water, 80% aqueous ethanol, ethanol and ether
  6. customis dried

Sources & evidence

ORD record
ord-f3aa20de38694568800f326f438cb238
Source dataset
uspto-grants-1980_01
Patent number
US04185033

Reaction notes

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