Chloride → HCID 67313482, Verbindung

HRID 1672417Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1672417
[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][C:22]([C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)=[O:23].C(=O)(O)[O-].[Na+].[Cl-]>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[C:22]([C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)=[O:23]

Komponenten

7

Edukt 4

HCID 312ChlorideHCID 516892Sodium Bicarbonate2×HCID 2799903HCID 2799903, VerbindungHCID 67313799HCID 67313799, Verbindung

Produkt 1

HCID 67313482HCID 67313482, VerbindungAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

A mixture of 56 mg (0.25 mmol) of 2,4-dichloro-N-hydroxybenzenecarboximidoyl chloride, 60 mg (0.25 mmol) of 3-(2-chlorophenyl)-1-(3-pyridyl)-2-propyn-1-one, and 30 mg (0.36 mmol) of sodium bicarbonate in 2.5 mL of isopropyl alcohol was heated at 55° C. overnight with shaking. An additional 30 mg of carboximidoyl chloride and 15 mg of sodium bicarbonate was then added, and the mixture was heated for another 20 hrs. 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 90 mg (0.21 mmol) of 5-(2-chlorophenyl)-3-(2,4-dichlorophenyl)-4-[(3-pyridyl)carbonyl]isoxazole. 1H NMR (CDCl3): δ 7.16 (m, 1), 7.60 (m,2), 7.92 (m, 1), 8.53 (br d, 1), and 8.74 ppm (br s, 1). MS m/z: 428.9 (M+H).

Aufarbeitung

  1. temperaturethe mixture was heated for another 20 hrs
  2. temperatureThe reaction mixture was cooled
  3. washwashed with saturated sodium bicarbonate
  4. dry with materialThe ether fraction was dried over magnesium sulfate
  5. filtrationThe drying agent was filtered off
  6. customthe ether was removed by rotoevaporation
  7. customThe crude product was purified by prep TLC

Quellen und Nachweise

ORD-Eintrag
ord-6383957b0737494cbe61a41938e7cfb5
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07998983B2

Notizen zur Reaktion

Wird geladen…