Hydrochloric Acid → HCID 9968373, compound

HRID 351125Notes

Reaction equation

HRID 351125 reaction equation
[C:1]1([S:7]([NH2:10])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:17][C:18]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:19]=1[C:20](Cl)=[O:21].Cl>O1CCOCC1.O>[Cl:17][C:18]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:19]=1[C:20]([NH:10][S:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:9])=[O:8])=[O:21]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7370BenzenesulfonamideHCID 11430Potassium CarbonateHCID 666452,4-Dichlorobenzoyl chloride

Product 1

HCID 9968373HCID 9968373, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a mixture of phenylsulfonamide (0.16 mol; 25.12 g) and potassium carbonate (0.2 mol; 27.6 g) in 500 mL dioxane is added dropwise 2,4-dichlorobenzoyl chloride (0.13 mole; 18.0 mL). The mixture is warmed to reflux under nitrogen for 16 hr. The reaction is then diluted with water (500 mL), neutralized to pH 5 with concentrated hydrochloric acid, and extracted 3 times with ethyl acetate. The combined ethyl acetate layers are washed with saturated aqueous sodium chloride, dried over sodium sulfate and concentrated under reduced pressure to a white solid. The solid residue is subjected to silica gel chromatography, eluting with dichloromethane containing from 0–5% methanol. Fractions containing the product are combined and concentrated under reduced pressure to provide the title compound.

Workup

  1. temperatureThe mixture is warmed
  2. temperatureto reflux under nitrogen for 16 hr
  3. extractionextracted 3 times with ethyl acetate
  4. washThe combined ethyl acetate layers are washed with saturated aqueous sodium chloride
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure to a white solid
  7. washeluting with dichloromethane containing from 0–5% methanol
  8. additionFractions containing the product
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9a689016a91146058152c718fb68f710
Source dataset
uspto-grants-2007_02
Patent number
US07183320B2

Reaction notes

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