Sulfuric Acid → 2-Nitrobenzenediazonium Bisulfate

HRID 1281060Notes

Reaction equation

HRID 1281060 reaction equation
[S:1](=[O:5])(=[O:4])([OH:3])[OH:2].[N+:6]([C:9]1[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=1[NH2:11])([O-:8])=[O:7].[N:16]([O-])=O.[Na+]>O>[S:1](=[O:3])(=[O:2])([OH:5])[O-:4].[N+:6]([C:9]1[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=1[N+:11]#[N:16])([O-:8])=[O:7]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 69462-NitroanilineHCID 23668193Sodium Nitrite

Product 1

HCID 124275962-Nitrobenzenediazonium Bisulfate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

To a 500 mL three-necked flask fitted with a mechanical stirrer are added 65 g of concentrated sulfuric acid and 41.4 g of 2-nitroaniline. After heating to 75° C., 164 g of water is added at which time the temperature is reduced to 0° C. Sodium nitrite (54 g, 40 wt %) is added over two hours while maintaining the solution at 0-5° C. The diazonium salt solution (292 g) is then filtered and stored at −15° C. until use.

Workup

  1. customTo a 500 mL three-necked flask fitted with a mechanical stirrer
  2. customis reduced to 0° C
  3. temperaturewhile maintaining the solution at 0-5° C
  4. filtrationThe diazonium salt solution (292 g) is then filtered
  5. customstored at −15° C. until use

Sources & evidence

ORD record
ord-3fe9b33876e54c8b9e5f49898cfdc989
Source dataset
uspto-grants-2002_09
Patent number
US06451887B1

Reaction notes

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