Nitrobenzene → 3-Nitrobenzenesulfonyl chloride

HRID 846304Notes

Reaction equation

HRID 846304 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)([O-:3])=[O:2].[Cl:10][S:11](O)(=[O:13])=[O:12]>S(=O)(=O)(O)N>[N+:1]([C:4]1[CH:9]=[C:8]([S:11]([Cl:10])(=[O:13])=[O:12])[CH:7]=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 7416NitrobenzeneHCID 24638Chlorosulfonic acid

Product 1

HCID 84763-Nitrobenzenesulfonyl chlorideYield 87.8%

Reagents, catalysts & solvents 1

HCID 5987Sulfamic AcidCatalyst

Conditions

Temperature
105 °C

Procedure

123.1 g (1.0 mol) of nitrobenzene are allowed to run rapidly into 582.5 g (5.0 mol) of chlorosulfonic acid and 1 g of sulfamic acid at room temperature. The mixture is then heated to 105° C. and stirred at this temperature for 6 hours. For working up, the reaction mixture is dripped into ice water. The precipitated crystals are filtered off with suction and washed with water. 194.6 g of dry 3-nitrobenzenesulfonyl chloride having a melting point of 59°-61° C., corresponding to a yield of 87.8% of theory, are obtained.

Workup

  1. filtrationThe precipitated crystals are filtered off with suction
  2. washwashed with water

Sources & evidence

ORD record
ord-2d7bea3a24eb43c7abc92aa29c55059e
Source dataset
uspto-grants-1992_08
Patent number
US05136043

Reaction notes

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