Sulfuric Acid → 4-Trifluoromethyl-2-nitrobenzenediazonium Bisulfate

HRID 2296839Notes

Reaction equation

HRID 2296839 reaction equation
[S:1](=[O:5])(=[O:4])([OH:3])[OH:2].[NH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][C:8]=1[N+:17]([O-:19])=[O:18].[N:20]([O-])=O.[Na+]>O>[S:1](=[O:3])(=[O:2])([OH:5])[O-:4].[F:14][C:13]([F:16])([F:15])[C:10]1[CH:11]=[CH:12][C:7]([N+:6]#[N:20])=[C:8]([N+:17]([O-:19])=[O:18])[CH:9]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 67865Benzenamine, 2-nitro-4-(trifluoromethyl)-HCID 23668193Sodium Nitrite

Product 1

HCID 111861204-Trifluoromethyl-2-nitrobenzenediazonium Bisulfate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

To a 500 mL three-necked flask equipped with a mechanical stirrer is added 99.5 g of concentrated sulfuric acid and 62.5 g of 4-trifluoro-2-nitroaniline (or 4-amino-3-nitro benzotrifluoride). After heating to 75° C., 200 g of water is added at which time the temperature is reduced to 0° C. Sodium nitrite solution (52.9 g, 40% by weight in water) is added over two hours while maintaining the temperature at 0-5° C. The title diazonium salt solution (351 g) is filtered and stored at −15° C. for later use.

Workup

  1. customTo a 500 mL three-necked flask equipped with a mechanical stirrer
  2. customis reduced to 0° C
  3. temperaturewhile maintaining the temperature at 0-5° C
  4. filtrationThe title diazonium salt solution (351 g) is filtered
  5. customstored at −15° C. for later use

Sources & evidence

ORD record
ord-0826520c93554e2cbd5419997a019b1d
Source dataset
uspto-grants-2002_12
Patent number
US06489383B1

Reaction notes

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