Hydrochloric Acid → 2-Phenyl-ethenesulfonic acid 4-chloro-2-fluoro-benzoylamide

HRID 1272357Notes

Reaction equation

HRID 1272357 reaction equation
[C:1]1([CH:7]=[CH:8][S:9]([NH2:12])(=[O:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:13][C:14]1[CH:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[C:16]([F:23])[CH:15]=1.O.Cl>O1CCOCC1>[Cl:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([NH:12][S:9]([CH:8]=[CH:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)(=[O:10])=[O:11])=[O:19])=[C:16]([F:23])[CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 2575012-PhenylethenesulfonamideHCID 27736014-Chloro-2-fluorobenzoyl chloride

Product 1

HCID 691169662-Phenyl-ethenesulfonic acid 4-chloro-2-fluoro-benzoylamideYield 79.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-phenyl-ethenesulfonic acid amide (500 mg, 2.7 mmol) in dioxane (25 ml) sodium hydride (197 mg, 55% dispersion in mineral oil) were added and the mixture was stirred at room temperature for 30 minutes. 4-Chloro-2-fluoro-benzoyl chloride (527 mg, 2.7 mmol) were added and the mixture was stirred at room temperature overnight. After addition of water (50 ml) the pH was adjusted to 7 with 1 N HCl and the mixture was extracted with ethyl acetate (3 times 50 ml). The combined organic phases were dried over Na2SO4 and concentrated in vacuo. Preparative HPLC (RP18, methanol-water-gradient) returned the title compound (730 mg, 79% yield) as a white solid.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. extractionthe mixture was extracted with ethyl acetate (3 times 50 ml)
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-17b7baa4b60f45e5925d19bf52b262d1
Source dataset
uspto-grants-2007_04
Patent number
US07208526B2

Reaction notes

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