Dimethylformamide → 4-Chloro-2-nitrophenylsulfonyl chloride

HRID 513721Notes

Reaction equation

HRID 513721 reaction equation
CN(C=O)C.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([S:13](O)(=[O:15])=[O:14])=[C:9]([N+:17]([O-:19])=[O:18])[CH:8]=1.O=S(Cl)[Cl:22]>>[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([Cl:22])(=[O:15])=[O:14])=[C:9]([N+:17]([O-:19])=[O:18])[CH:8]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 4268414-Chloro-2-nitrobenzene-1-sulfonic acid

Product 1

HCID 206314-Chloro-2-nitrophenylsulfonyl chloride

Conditions

Temperature
90 °C

Procedure

DMF (0.06 ml, cat) was added to a solution of 4-chloro-2-nitro-benzenesulfonic acid (600 mg, 2.5 mmol) in SOCl2 (3.1 ml) and the mixture was heated at 90° C. for 3 h. After cooling, the solvent was removed in vacuo. The mixture was diluted with water and extracted repeatedly with chloroform. The combined organic layers were washed with saturated NaHCO3 solution, dried (Na2SO4) and concentrated in vacuo to give the title compound (560 mg) which was used in the next step without further purification. The structure was confirmed by 1H NMR.

Workup

  1. temperatureAfter cooling
  2. customthe solvent was removed in vacuo
  3. additionThe mixture was diluted with water
  4. extractionextracted repeatedly with chloroform
  5. washThe combined organic layers were washed with saturated NaHCO3 solution
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fdc834d4f793418ca15acaf64698d658
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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