Benzoyl chloride, 3-(chlorosulfonyl)- → 3-[3-(3,5-difluorophenyl)-2-(1,3-dihydrobenzimidazol-2-ylidene)-3-oxopropanoyl]benzenesulfonyl chloride

HRID 2423230Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2423230
[F:1][C:2]1[CH:3]=[C:4]([C:9](=[O:20])[CH:10]=[C:11]2[NH:15][C:14]3[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=3[NH:12]2)[CH:5]=[C:6]([F:8])[CH:7]=1.[Cl:21][S:22]([C:25]1[CH:26]=[C:27]([CH:31]=[CH:32][CH:33]=1)[C:28](Cl)=[O:29])(=[O:24])=[O:23]>O1CCOCC1>[F:1][C:2]1[CH:3]=[C:4]([C:9](=[O:20])[C:10](=[C:11]2[NH:12][C:13]3[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=3[NH:15]2)[C:28]([C:27]2[CH:26]=[C:25]([S:22]([Cl:21])(=[O:24])=[O:23])[CH:33]=[CH:32][CH:31]=2)=[O:29])[CH:5]=[C:6]([F:8])[CH:7]=1

Komponenten

4

Edukt 2

HCID 77671Benzoyl chloride, 3-(chlorosulfonyl)-HCID 1785203801-(3,5-difluorophenyl)-2-(1,3-dihydrobenzimidazol-2-ylidene)ethanone

Produkt 1

HCID 1785208713-[3-(3,5-difluorophenyl)-2-(1,3-dihydrobenzimidazol-2-ylidene)-3-oxopropanoyl]benzenesulfonyl chloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

1-(3,5-Difluorophenyl)-2-(1,3-dihydro-2H-benzimidazol-2-ylidene)ethanone and 3-(chlorosulfonyl)benzoyl chloride were heated under reflux in dioxane for 1 hour, followed by cooling. After dilution with ethyl acetate, the insoluble matter was separated by filtration. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography. This was further diluted with ethyl acetate, washed with an aqueous saturated sodium hydrogencarbonate solution and water successively, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to obtain 3-[3-(3,5-difluorophenyl)-2-(1,3-dihydro-2H-benzimidazol-2-ylidene)-3-oxopropanoyl]benzenesulfonyl chloride.

Aufarbeitung

  1. temperatureby cooling
  2. customAfter dilution with ethyl acetate, the insoluble matter was separated by filtration
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe resulting residue was purified by silica gel column chromatography
  5. additionThis was further diluted with ethyl acetate
  6. washwashed with an aqueous saturated sodium hydrogencarbonate solution and water successively
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-6fa8c20e49354e99b0a2c50164cbd249
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07960562B2

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