Water → 2-[2-Hydroxy-4-isopropylbenzoylamino]-N-(5-chloropyridin-2-yl)benzamide

HRID 644213Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 644213
COC[O:4][C:5]1[CH:29]=[C:28]([CH:30]([CH3:32])[CH3:31])[CH:27]=[CH:26][C:6]=1[C:7]([NH:9][C:10]1[CH:25]=[CH:24][CH:23]=[CH:22][C:11]=1[C:12]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][N:16]=1)=[O:13])=[O:8].C(O)(C(F)(F)F)=O.O>ClCCl>[OH:4][C:5]1[CH:29]=[C:28]([CH:30]([CH3:32])[CH3:31])[CH:27]=[CH:26][C:6]=1[C:7]([NH:9][C:10]1[CH:25]=[CH:24][CH:23]=[CH:22][C:11]=1[C:12]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][N:16]=1)=[O:13])=[O:8]

Komponenten

5

Edukt 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 685343382-[2-methoxymethyloxy-4-isopropylbenzoylamino]-N-(5-chloropyridin-2-yl)benzamide

Produkt 1

HCID 685329372-[2-Hydroxy-4-isopropylbenzoylamino]-N-(5-chloropyridin-2-yl)benzamideAusbeute 22 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirring solution of 2-[2-methoxymethyloxy-4-isopropylbenzoylamino]-N-(5-chloropyridin-2-yl)benzamide (5.74 g, 12.6 mmol) in dichloromethane (20 mL) was added TFA (100 mL) followed by water (100 mL). After stirring for 15 min, the solvents were removed in vacuo and the residue was partitioned between ethyl acetate (500 mL) and water (200 mL). At this point, the mixture was filtered to give 1.13 g (22%) of white solid. The filtrate was returned to a separatory funnel and the layers were separated. The organic phase was then washed with 1 M citric acid, once with brine, twice with saturated aq sodium bicarbonate, and once again with brine. The organic phase was then dried with MgSO4, filtered and concentrated to a volume of about 50 mL in vacuo. At this point, a significant amount of precipitate had formed; so the mixture was sonicated and filtered to give another 2.76 g (53%) of the title compound.

Aufarbeitung

  1. customthe solvents were removed in vacuo
  2. customthe residue was partitioned between ethyl acetate (500 mL) and water (200 mL)
  3. filtrationAt this point, the mixture was filtered

Quellen und Nachweise

ORD-Eintrag
ord-d634a7be0ebd4322a14dbd3f2d37353f
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07700628B2

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