Hydrochloric Acid → Benzenesulfonyl chloride, 4-chloro-3-nitro-

HRID 1439371Notes

Reaction equation

HRID 1439371 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N+:13]([O-:15])=[O:14].Cl>>[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([S:2]([Cl:1])(=[O:5])=[O:3])=[CH:9][C:8]=1[N+:13]([O-:15])=[O:14]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 69451-Chloro-2-nitrobenzeneHCID 24638Chlorosulfonic acid

Product 1

HCID 7323Benzenesulfonyl chloride, 4-chloro-3-nitro-

Conditions

Temperature
80 °C

Procedure

Under a nitrogen atmosphere, 350 ml. of chlorosulfonic acid was added to 236 g. (1.50 mole) of 2-chloronitrobenzene. The resulting green colored solution was heated for 18 hours at 80° C., then the temperature was increased to 140° C. and held at this temperature until HCl gas evolution ceased (about 90 minutes). The reaction mixture was then cooled to 25° C. and slowly poured onto 4 liters of ice. After stirring for 20 minutes the mixture was filtered to obtain a pale yellow solid. The filter cake was sucked dry then allowed to dry in a vacuum oven at 25° C. overnight, m.p. 37°-38° C., yield 362.3 g. (94%).

Workup

  1. temperaturethe temperature was increased to 140° C.
  2. custom(about 90 minutes)
  3. temperatureThe reaction mixture was then cooled to 25° C.
  4. filtrationwas filtered
  5. customto obtain a pale yellow solid
  6. customThe filter cake was sucked dry
  7. customto dry in a vacuum oven at 25° C. overnight

Sources & evidence

ORD record
ord-be36cfd5ad074e27bce5f411e1fe4565
Source dataset
uspto-grants-1977_11
Patent number
US04059584

Reaction notes

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