Hydrochloric Acid → 5-Azidoisophthalic acid

HRID 522189Notes

Reaction equation

HRID 522189 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:11]([OH:13])=[O:12])[CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].Cl.N([O-])=O.[Na+].[N-:19]=[N+:20]=[N-].[Na+]>O>[N:1]([C:2]1[CH:3]=[C:4]([C:11]([OH:13])=[O:12])[CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8])=[N+:19]=[N-:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 33557Sodium AzideHCID 668335-Aminoisophthalic acidHCID 23668193Sodium Nitrite

Product 1

HCID 30366025-Azidoisophthalic acidYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Conditions

Temperature
2.5 °C

Procedure

73 mmol of 5-aminoisophtalic acid were placed in a beaker together with 100 mL of water. 18 mL of HCl (37%) were added dropwise. The mixture was cooled in an ice bath at 0-5° C. 75.3 mmol of NaNO2 were dissolved in 25 mL of distilled water and added dropwise to the mixture, stirring it for 30 minutes. Then, 73 mmol of NaN3 were dissolved in 25 mL of distilled water and added dropwise to the mixture. A solid was formed and gas evolution was observed, making it difficult to keep the stirring. The mixture was stirred until the evolution of gas was no longer detected. The product was then filtered off, washed with distilled water, and dried at room temperature. Yield: 85%. M.p.: 250° C.

Workup

  1. additionadded dropwise to the mixture
  2. additionadded dropwise to the mixture
  3. customA solid was formed
  4. stirringThe mixture was stirred until the evolution of gas
  5. filtrationThe product was then filtered off
  6. washwashed with distilled water
  7. customdried at room temperature

Sources & evidence

ORD record
ord-b506f32396e7443c81d0632c6b85f19d
Source dataset
uspto-grants-2016_05
Patent number
US09328199B2

Reaction notes

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