Water → 2-[5-Chloro-3-(4-chloro-3-trifluoromethyl-benzenesulfonylamino)-pyridine-2-carbonyl]benzoic acid

HRID 1898117Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1898117
[Cl:1][C:2]1[CH:3]=[C:4]([N:19]([S:23]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([C:33]([F:36])([F:35])[F:34])[CH:27]=2)(=[O:25])=[O:24])COC)[C:5]([C:8]([C:10]2[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=2[C:12]([OH:14])=[O:13])=[O:9])=[N:6][CH:7]=1.O>Cl.O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:19][S:23]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([C:33]([F:36])([F:35])[F:34])[CH:27]=2)(=[O:24])=[O:25])[C:5]([C:8]([C:10]2[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=2[C:12]([OH:14])=[O:13])=[O:9])=[N:6][CH:7]=1

Komponenten

5

Edukt 2

HCID 962WaterHCID 579423682-{5-Chloro-3-[(4-chloro-3-trifluoromethyl-benzenesulfonyl)-methoxymethyl-amino]-pyridine-2-carbonyl}-benzoic acid

Produkt 1

HCID 116565312-[5-Chloro-3-(4-chloro-3-trifluoromethyl-benzenesulfonylamino)-pyridine-2-carbonyl]benzoic acidAusbeute 42,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of 2-{5-Chloro-3-[(4-chloro-3-trifluoromethyl-benzenesulfonyl)-methoxymethyl-amino]-pyridine-2-carbonyl}-benzoic acid (150 mg, 0.27 mmol) in 3 ml of 4M HCl in dioxane and 1 mL of water was refluxed for 2 hours. After cooling to room temperature the mixture was concentrated and then diluted with water. Sodium bicarbonate was added until pH was 6. The mixture was extracted with ethyl acetate, dried and concentrated. The residue was further purified via flash column (70% ethyl acetate in hexane) to afford 60 mg of title compound as an off white solid. MS: (M+H)/z=519.4.

Aufarbeitung

  1. concentrationwas concentrated
  2. additiondiluted with water
  3. additionSodium bicarbonate was added until pH was 6
  4. extractionThe mixture was extracted with ethyl acetate
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was further purified via flash column (70% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-45b60cb85a3548f1b55e0cd4340e21cf
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08519135B2

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