Hydrochloric Acid → 62083-99-2

HRID 269373Notes

Reaction equation

HRID 269373 reaction equation
[S:1]([OH:11])(=[O:10])([C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1)=[O:2].N([O-])=O.[Na+].Cl.S(=O)(=O)(O)[NH2:18].S(C[NH:27][C:28]1[CH:36]=[CH:35][CH:34]=[CH:33][C:29]=1[C:30]([OH:32])=[O:31])(O)(=O)=O.[OH-].[Na+]>O>[NH2:27][C:28]1[CH:36]=[CH:35][C:34]([N:18]=[N:9][C:6]2[CH:5]=[CH:4][C:3]([S:1]([OH:11])(=[O:10])=[O:2])=[CH:8][CH:7]=2)=[CH:33][C:29]=1[C:30]([OH:32])=[O:31]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 5987Sulfamic AcidHCID 8479Sulfanilic acidHCID 14798Sodium HydroxideHCID 23668193Sodium NitriteHCID 595474082-[(Sulfomethyl)amino]benzoic acid

Product 1

HCID 7139015262083-99-2

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Sulfanilic acid (8.65 g, 0.05 mol) and sodium nitrite (3.8 g) were dissolved in water (pH 8, 100 ml). This solution was added to a beaker containing ice (30 g) and concentrated hydrochloric acid (15 ml). After stirring for 15 minutes, sulfamic acid (0.5 g) was added. This diazonium salt solution was added to a solution of the 2-((sulfomethyl)amino)benzoic acid prepared in stage 1 in water (150 ml) at 0 to 5° C. The reaction mixture was stirred at 0-5° C. for 1.5 hours while the pH of the reaction medium was maintained at pH 4 to 4.5 by the addition of dilute sodium hydroxide solution. When the diazonium salt had been consumed the product was precipitated by the addition of 2M hydrochloric acid. The precipitate was collected by filtration and then dissolved in water (200 ml) adjusted to pH 12 with lithium hydroxide. The resultant solution was stirred at 70° C. for 2 hours, maintaining the pH by periodic addition of 2M lithium hydroxide solution. After cooling, the reaction mixture was adjusted to pH6 with 2M hydrochloric acid. The precipitated dye was collected by filtration as a brown solid (18 g).

Workup

  1. additionThis solution was added to a beaker
  2. stirringThe reaction mixture was stirred at 0-5° C. for 1.5 hours while the pH of the reaction medium
  3. customWhen the diazonium salt had been consumed the product
  4. customwas precipitated by the addition of 2M hydrochloric acid
  5. filtrationThe precipitate was collected by filtration
  6. dissolutiondissolved in water (200 ml)
  7. stirringThe resultant solution was stirred at 70° C. for 2 hours
  8. temperaturemaintaining the pH
  9. additionby periodic addition of 2M lithium hydroxide solution
  10. temperatureAfter cooling
  11. filtrationThe precipitated dye was collected by filtration as a brown solid (18 g)

Sources & evidence

ORD record
ord-d734d240d62744a09c4706e1831896d2
Source dataset
uspto-grants-2008_11
Patent number
US07446184B2

Reaction notes

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