Methane → HCID 131711198, compound

HRID 2419605Notes

Reaction equation

HRID 2419605 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.Cl.[C:28](Cl)(Cl)=[S:29].C>O>[Na+:1].[Na+:1].[Na+:1].[N: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:20])=[O:21])=[CH:10]2)=[C:28]=[S:29]

Participants

6

Reactant 4

HCID 297MethaneHCID 313Hydrochloric AcidHCID 10040ThiophosgeneHCID 1018991,3,6-Naphthalenetrisulfonic acid, 8-amino-, sodium salt (1:?)

Product 1

HCID 131711198HCID 131711198, compoundYield 129.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 78.0 g of 8-amino-1,3,6-naphthalenetrisulfonic acid trisodium salt in 500 ml of water is added 17.0 ml of concentrated hydrochloric acid. The solution is cooled to room temperature and 29 g of thiophosgene is added with vigorous stirring. Stirring is continued for 2.5 hours at room temperature. The mixture is treated with activated charcoal, filtered through diatomaceous earth and evacuated by water pump to remove excess thiophosgene. The filtrate is neutralized with 5N sodium hydroxide and evaporated in vacuo to 250 ml. The solution is allowed to crystallize at room temperature, then in an ice bath. The mixture is filtered and the precipitate is washed with ice water, acetone and ether to give a yellow powder. The power is recrystallized from 110 ml of water by warming, then cooling and seeding. The product is collected after standing and the resulting filtrate is concentrated and recrystallized as above. The products are combined and dried by conventional means to yield 36.9 g of 8-isothiocyanato-1,3,6-naphthalenetrisulfonic acid trisodium salt.

Workup

  1. filtrationfiltered through diatomaceous earth
  2. customevacuated by water pump
  3. customto remove excess thiophosgene
  4. customevaporated in vacuo to 250 ml
  5. customto crystallize at room temperature
  6. filtrationThe mixture is filtered
  7. washthe precipitate is washed with ice water, acetone and ether
  8. customto give a yellow powder
  9. customThe power is recrystallized from 110 ml of water
  10. temperatureby warming
  11. temperaturecooling
  12. customThe product is collected
  13. concentrationthe resulting filtrate is concentrated
  14. customrecrystallized as above
  15. customdried by conventional means

Sources & evidence

ORD record
ord-4fa9c60b11e34545a450fc2db8e4aa66
Source dataset
uspto-grants-1978_08
Patent number
US04107201

Reaction notes

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