1-Chloro-2-nitrobenzene → Benzenesulfonyl chloride, 4-chloro-3-nitro-

HRID 846306Notes

Reaction equation

HRID 846306 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[Cl:11][S:12](O)(=[O:14])=[O:13]>S(=O)(=O)(O)N.O>[N+:8]([C:3]1[CH:4]=[C:5]([S:12]([Cl:11])(=[O:14])=[O:13])[CH:6]=[CH:7][C:2]=1[Cl:1])([O-:10])=[O:9]

Participants

5

Reactant 2

HCID 69451-Chloro-2-nitrobenzeneHCID 24638Chlorosulfonic acid

Product 1

HCID 7323Benzenesulfonyl chloride, 4-chloro-3-nitro-Yield 90.9%

Reagents, catalysts & solvents 2

HCID 5987Sulfamic AcidCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

157.6 g (1.0 mol) of 2-chloronitrobenzene are added to 699 g (6.0 mol) of chlorosulfonic acid and 2 g of sulfamic acid such that the temperature does not exceed 40° C. After addition is complete, the mixture is heated to 100° C. and stirred at this temperature for 6 hours. The reaction mixture is dripped into water at 15° C., and the precipitated crystals are filtered off with suction and washed with water. 236.2 g of 2-nitrochlorobenzene-4-sulfonyl chloride having a water content of 1.5%, corresponding to 232.7 g of 2-nitrochlorobenzene-4-sulfonyl chloride (90.8% of theory), are obtained.

Workup

  1. customdoes not exceed 40° C
  2. additionAfter addition
  3. filtrationthe precipitated crystals are filtered off with suction
  4. washwashed with water

Sources & evidence

ORD record
ord-783a86c711f8484797356ab7a6aed1b7
Source dataset
uspto-grants-1992_08
Patent number
US05136043

Reaction notes

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