Nitrobenzene → 3-Nitrobenzenesulfonyl chloride

HRID 1648603Notes

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(Cl)(Cl)=O>>[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

Reactant 3

HCID 7416Nitrobenzene

HCID 24386Thionyl Chloride

HCID 24638Chlorosulfonic acid

Product 1

HCID 84763-Nitrobenzenesulfonyl chlorideYield 107.2%

Conditions

Temperature: 70 °C

Procedure

123.1 g (1.0 mol) of nitrobenzene was added dropwise at 112° C. to 521.0 g (4.4 mol) of chlorosulfonic acid over the course of 4 hours. The mixture was then stirred at this temperature for 4 hours. After it had been cooled to 70° C., 110.0 g (0.92 mol) of thionyl chloride were added dropwise over the course of 2 hours. The reaction mixture was then stirred at this temperature until evolution of gas had ended. It was then cooled and discharged at 5° C. into ice-water. The precipitated 3-nitrobenzenesulfonyl chloride was then filtered off with suction and washed with water and with sodium hydrogen carbonate. 237.5 g of moist 3-nitrobenzenesulfonyl chloride having a purity of 89.9% were obtained in this manner. The dry content was 213.5 g, which corresponds to a yield of 96.3%.

Workup

stirringThe reaction mixture was then stirred at this temperature until evolution of gas
temperatureIt was then cooled
filtrationThe precipitated 3-nitrobenzenesulfonyl chloride was then filtered off with suction
washwashed with water and with sodium hydrogen carbonate

Sources & evidence

ORD record: ord-de9d81a04f4c4b55915380d1ceeb8385
Source dataset: uspto-grants-1995_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05436370

Reaction notes

Loading…