Sodium Bicarbonate → HCID 59759989, Verbindung

HRID 1010697Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1010697
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9](Cl)=[N:10][OH:11].[Cl:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]#[C:21][CH:22]([C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)[OH:23].C(=O)(O)[O-].[Na+]>C(O)(C)C.CCOCC>[Cl:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]1[O:11][N:10]=[C:9]([C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])[C:21]=1[CH:22]([C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)[OH:23]

Komponenten

6

Edukt 3

HCID 516892Sodium BicarbonateHCID 2799903HCID 2799903, VerbindungHCID 67313359HCID 67313359, Verbindung

Produkt 1

HCID 59759989HCID 59759989, VerbindungAusbeute 16,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

A mixture of 52 mg (0.23 mmol) of 2,4-dichloro-N-hydroxybenzenecarboximidoyl chloride, 50 mg (0.21 mmol) of 3-(2-chlorophenyl)-1-(3-pyridyl)-2-propyn-1-ol, and 30 mg (0.36 mmol) of sodium bicarbonate in 3 mL of isopropyl alcohol was heated at 55° C. overnight with shaking. The reaction mixture was cooled, diluted with ether, and then washed with saturated sodium bicarbonate. The ether fraction was dried over magnesium sulfate. The drying agent was filtered off, and the ether was removed by rotoevaporation. The crude product was purified by prep TLC to give 15 mg (0.035 mmol) of 5-(2-chlorophenyl)-3-(2,4-dichlorophenyl)-4-[(3-pyridyl)hydroxymethyl]isoxazole. 1H NMR (CDCl3): δ 5.80 (br s, 1). MS m/z: 431.0 (M+H).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. washwashed with saturated sodium bicarbonate
  3. dry with materialThe ether fraction was dried over magnesium sulfate
  4. filtrationThe drying agent was filtered off
  5. customthe ether was removed by rotoevaporation
  6. customThe crude product was purified by prep TLC

Quellen und Nachweise

ORD-Eintrag
ord-3cbdb8f2939e48b794ecfcc4cc78c549
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07977341B2

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