2-Nitrotoluene → 4-Methyl-3-nitrobenzenesulfonyl chloride

HRID 1474419Notes

Reaction equation

HRID 1474419 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[N+:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH3:15])([O-:8])=[O:7]>>[CH3:15][C:10]1[CH:11]=[CH:12][C:13]([S:2]([Cl:1])(=[O:5])=[O:3])=[CH:14][C:9]=1[N+:6]([O-:8])=[O:7]

Participants

3

Reactant 2

HCID 69442-NitrotolueneHCID 24638Chlorosulfonic acid

Product 1

HCID 5606384-Methyl-3-nitrobenzenesulfonyl chloride

Conditions

Temperature
85 °C

Procedure

Placed chlorosulfonic acid (128 mL, 1.91 mmol) in a 500 mL four necked round bottomed flask. Then added 2-nitro toluene (65 mL, 0.547 mmol) drop wise, under stirring in 25 minutes at 25° C. The reaction mass was heated at 85° C. for 3 hours. Quenched the reaction mass into ice cold water and extracted with ethylacetate (4×250 mL), the combined organic layer was washed with brine solution (1×100 mL), dried over anhydrous sodium sulfate and solvent was removed under reduced pressure to obtain syrupy product. Yield: 109.5 grams.

Workup

  1. customQuenched the reaction mass into ice cold water
  2. extractionextracted with ethylacetate (4×250 mL)
  3. washthe combined organic layer was washed with brine solution (1×100 mL)
  4. dry with materialdried over anhydrous sodium sulfate and solvent
  5. customwas removed under reduced pressure
  6. customto obtain syrupy product

Sources & evidence

ORD record
ord-660f7fd6cda14c5689b38db5ac9e8aa2
Source dataset
uspto-grants-2015_04
Patent number
US09018231B2

Reaction notes

Loading…