Hydrochloric Acid → HCID 20443396, compound

HRID 1632161Notes

Reaction equation

HRID 1632161 reaction equation
[Br:1][C:2]1[C:10]([C:11]([OH:13])=[O:12])=[C:9]([Br:14])[C:8](N)=[C:7]([Br:16])[C:3]=1[C:4]([OH:6])=[O:5].N([O-])=O.[Na+].[C-:21]#[N:22].[Na+].Cl>S(=O)(=O)(O)O.O.[Cu]>[Br:1][C:2]1[C:10]([C:11]([OH:13])=[O:12])=[C:9]([Br:14])[C:8]([C:21]#[N:22])=[C:7]([Br:16])[C:3]=1[C:4]([OH:6])=[O:5]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8929Sodium CyanideHCID 184324275-Amino-2,4,6-tribromo-1,3-benzenedicarboxylic acidHCID 23668193Sodium Nitrite

Product 1

HCID 20443396HCID 20443396, compoundYield 55%

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolvent

Procedure

2,4,6-Tribromo-5-amino-isophthalic acid (232 g; 0.555 mole) is dissolved in concentrated sulfuric acid (500 ml) and the solution is then cooled by means of an ice-bath to a temperature between 0° and 5° C. Sodium nitrite (77 g; 1.11 mole) is then added portionwise over 1 hour while maintaining the temperature at 0°-5° C., and the mixture is stirred for a further 2 hours at that temperature. The mixture is then slowly poured over ice, with stirring, and the excess sodium nitrite is destroyed with a sufficient amount of urea solution. While still maintaining the temperature at 0°-5° C., the suspension is neutralized at pH 6 by addition of 5N sodium hydroxide. The mixture is then added to a solution of cuprous chloride (69 g; 0.694 mole) and sodium cyanide (89 g; 1.82 mole) in 1 liter water, and the solution is stirred overnight at room temperature. The pH of the solution is adjusted to 3 by addition of hydrochloric acid, the copper salt precipitate is suction filtered, and the pH is adjusted to 1 with hydrochloric acid. The solution is cooled in an ice-bath and stirring is maintained for a further 16 hours. The resulting precipitate is suction filtered; it is then taken up into 400 ml water, with stirring, plus a sufficient amount of sodium hydroxide for dissolution and neutral pH. The solution is decolorized by stirring for 1 hour with charcoal 3 SA, after which the charcoal is filtered off, and the material is precipitated with dilute hydrochloric acid to give, after suction filtering and washing with a small amount of water, 130 g of white product (Yield: 55%).

Workup

  1. temperaturethe solution is then cooled by means of an ice-bath to a temperature between 0° and 5° C
  2. temperaturewhile maintaining the temperature at 0°-5° C.
  3. additionThe mixture is then slowly poured over ice
  4. stirringwith stirring
  5. customthe excess sodium nitrite is destroyed with a sufficient amount of urea solution
  6. temperatureWhile still maintaining the temperature at 0°-5° C.
  7. additionthe suspension is neutralized at pH 6 by addition of 5N sodium hydroxide
  8. stirringthe solution is stirred overnight at room temperature
  9. filtrationfiltered
  10. temperatureThe solution is cooled in an ice-bath
  11. stirringstirring
  12. temperatureis maintained for a further 16 hours
  13. filtrationfiltered
  14. stirringwith stirring
  15. dissolutiona sufficient amount of sodium hydroxide for dissolution and neutral pH
  16. stirringby stirring for 1 hour with charcoal 3 SA
  17. filtrationafter which the charcoal is filtered off
  18. customthe material is precipitated with dilute hydrochloric acid
  19. customto give
  20. filtrationafter suction filtering

Sources & evidence

ORD record
ord-3128f76a88d94ce9a8c857a74168dd72
Source dataset
uspto-grants-1984_10
Patent number
US04474747

Reaction notes

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