5-Nitroisophthaloyl chloride → 8,8'-[(5-Nitro-1,3-phenylene)bis(carbonylimino)]-di-1,3,6-naphthalenetrisulfonic acid hexasodium salt

HRID 867136

Reaction equation

HRID 867136 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.[OH2:27].[OH2:28].[OH2:29].[C:30]([O-])(=O)[CH3:31].[Na+].[N+:35]([C:38]1[CH:39]=[C:40]([C:47](Cl)=[O:48])[CH:41]=[C:42]([CH:46]=1)[C:43](Cl)=[O:44])([O-:37])=[O:36]>O>[Na+:1].[Na+:1].[Na+:1].[Na+:1].[Na+:1].[Na+:1].[N+:35]([C:38]1[CH:39]=[C:40]([C:47]([NH:4][C:5]2[CH:6]=[C:7]([S:23]([O-:26])(=[O:24])=[O:25])[CH:8]=[C:31]3[C:30]=2[C:11]([S:19]([O-:29])(=[O:28])=[O:27])=[CH:12][C:13]([S:15]([O-:18])(=[O:16])=[O:17])=[CH:14]3)=[O:48])[CH:41]=[C:42]([C:43]([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])[CH:46]=1)([O-:37])=[O:36]

Participants

5

Reactant 3

HCID 834515-Nitroisophthaloyl chlorideHCID 1018991,3,6-Naphthalenetrisulfonic acid, 8-amino-, sodium salt (1:?)HCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 1317111748,8'-[(5-Nitro-1,3-phenylene)bis(carbonylimino)]-di-1,3,6-naphthalenetrisulfonic acid hexasodium saltYield 252%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 13.75 g of 8-amino-1,3,6-naphthalenetrisulfonic acid trisodium salt and 4.6 g of sodium acetate trihydrate in 100 ml of water in a 500 ml baffle flask is added 4.10 g of powdered 5-nitroisophthaloyl chloride. The mixture is stirred vigorously at room temperature for one hour then is filtered through diatomaceous earth. The filtrate is concentrated to 50 ml, then warmed, acidified with 0.5 ml of concentrated hydrochloric acid and diluted with 50 ml of hot ethanol. The product is crystallized on cooling with scratching and is collected by filtration, then washed with 25 ml of 55% aqueous ethanol and 60 ml of ethanol. Additional product is obtained from the filtrate in the same manner. The total product is dried by conventional means to give 13.8 g of 8,8'-[(5-nitro-1,3-phenylene)bis(carbonylimino)]-di-1,3,6-naphthalenetrisulfonic acid hexasodium salt.

Workup

  1. filtrationthen is filtered through diatomaceous earth
  2. concentrationThe filtrate is concentrated to 50 ml
  3. temperaturewarmed
  4. additiondiluted with 50 ml of hot ethanol
  5. customThe product is crystallized
  6. temperatureon cooling
  7. filtrationis collected by filtration
  8. washwashed with 25 ml of 55% aqueous ethanol and 60 ml of ethanol
  9. customAdditional product is obtained from the filtrate in the same manner
  10. customThe total product is dried by conventional means

Sources & evidence

ORD record
ord-75d668475828472f91af17412ff87d3e
Source dataset
uspto-grants-1978_07
Patent number
US04102917

Linked notes

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