Sulfuric Acid → Benzene, 1,3-dichloro-5-nitro-

HRID 972666Notes

Reaction equation

HRID 972666 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[C:5]([Cl:12])[C:3]=1N.C(O)(C)C.S(=O)(=O)(O)O.N([O-])=O.[Na+]>O>[Cl:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[C:5]([Cl:12])[CH:3]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 3776IsopropanolHCID 74302,6-Dichloro-4-nitroanilineHCID 23668193Sodium Nitrite

Product 1

HCID 12064Benzene, 1,3-dichloro-5-nitro-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

207 parts of 2,6-dichloro-4-nitro-aniline are introduced into 180 parts of isopropanol and 300 parts of water and 200 parts of concentrated sulfuric acid (98 percent strength by weight) are then added to the mixture. A solution of 125 parts of NaNO2 in 175 parts of water is run in at 50° C. resulting in the evolution of nitrogen. The mixture is cooled, 400 parts of water are added and the product is filtered off. 192 parts (a practically quantitative yield) of 3,5-dichloro-nitro-benzene, of melting point 60°-62° C., are obtained.

Workup

  1. additionare then added to the mixture
  2. customis run in at 50° C.
  3. customresulting in the evolution of nitrogen
  4. temperatureThe mixture is cooled
  5. filtrationthe product is filtered off

Sources & evidence

ORD record
ord-6fb15a5bb167445ca3307d9f088d41df
Source dataset
uspto-grants-1977_10
Patent number
US04053527

Reaction notes

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