Methane → 8-Isothiocyanato-1,3,6-naphthalenetrisulfonic acid

HRID 280879

Reaction equation

HRID 280879 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([S:20]([OH:23])(=[O:22])=[O:21])[CH:5]=[C:6]2[C:11]=1[C:10]([S:12]([OH:15])(=[O:14])=[O:13])=[CH:9][C:8]([S:16]([OH:19])(=[O:18])=[O:17])=[CH:7]2.C1C(N=NC2C(=O)N(C3C=C[C:41]([S:44]([O-])(=O)=O)=CC=3)N=C2C([O-])=O)=CC=C(S([O-])(=O)=O)C=1.[Na+].[Na+].[Na+].C(Cl)(Cl)=S.C>O.Cl>[N:1]([C:2]1[CH:3]=[C:4]([S:20]([OH:23])(=[O:22])=[O:21])[CH:5]=[C:6]2[C:11]=1[C:10]([S:12]([OH:15])(=[O:14])=[O:13])=[CH:9][C:8]([S:16]([OH:19])(=[O:17])=[O:18])=[CH:7]2)=[C:41]=[S:44]

Participants

7

Reactant 4

HCID 297MethaneHCID 10040ThiophosgeneHCID 649518-Aminonaphthalene-1,3,6-trisulfonic acidHCID 164825Tartrazine

Product 1

HCID 184135668-Isothiocyanato-1,3,6-naphthalenetrisulfonic acid

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

To a solution of 32.0 g of 8-amino-1,3,6-naphthalenetrisulfonic acid, trisodium salt in 350 ml of water and 7.0 ml of concentrated hydrochloric acid was added 10.0 g of thiophosgene. The mixture was stirred 21/2 hours, treated with charcoal and filtered through diatomaceous earth. The filtrate was neutralized with 46 ml of 5N sodium hydroxide, chilled and the solid was collected and recrystallized from 40 ml of water by heating and then chilling in an ice bath. This solid was washed with ice water, acetone then ether and dried, giving 11.2 g of 8-isothiocyanato-1,3,6-naphthalenetrisulfonic acid, trisodium salt.

Workup

  1. filtrationfiltered through diatomaceous earth
  2. temperaturechilled
  3. customthe solid was collected
  4. customrecrystallized from 40 ml of water
  5. temperatureby heating
  6. temperaturechilling in an ice bath
  7. washThis solid was washed with ice water, acetone
  8. dry with materialether and dried

Sources & evidence

ORD record
ord-fb16acc28977421e87cfa5923f32400a
Source dataset
uspto-grants-1986_05
Patent number
US04591604

Linked notes

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