Sodium amide → HCID 66848663, Verbindung

HRID 2176158Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2176158
[NH2-].[Na+].Cl.[F:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][NH2:12])=[CH:7][CH:6]=1.Br[CH2:14][C:15]1[N:16]=[C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[O:18][CH:19]=1>O1CCCC1>[F:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]([CH2:14][C:15]2[N:16]=[C:17]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[O:18][CH:19]=2)[NH2:12])=[CH:7][CH:6]=1

Komponenten

5

Edukt 3

HCID 24533Sodium amideHCID 699814-Fluorophenylhydrazine hydrochlorideHCID 534214634-Bromomethyl-2-phenyl-oxazole

Produkt 1

HCID 66848663HCID 66848663, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A flask containing tetrahydrofuran (2.0 mL) was charged with sodium amide (152 mg, 3.69 mmol; Aldrich) and chilled to 0° C. (4-Fluorophenyl)hydrazine hydrochloride (400 mg, 2.46 mmol; Aldrich) was added in portions. After 5 minutes, the solid had completely dissolved and the ice bath was removed. Stirring was continued for 1 hour, then the solution was chilled again in an ice bath and 4-(bromomethyl)-2-phenyloxazole (586 mg, 2.46 mmol; Anichem) was added dropwise. After 30 minutes, the ice bath was removed and the reaction was heated to 50° C. overnight. The mixture was diluted with water (5 mL) and extracted with dichloromethane (2×10 mL). The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated in vacuo to afford the title product which was carried on without further purification: LC/MS (DCI/NH3) m/z 267 (M+H−NH3)+.

Aufarbeitung

  1. additionwas added in portions
  2. dissolutionthe solid had completely dissolved
  3. customthe ice bath was removed
  4. waitwas continued for 1 hour
  5. temperaturethe solution was chilled again in an ice bath
  6. waitAfter 30 minutes
  7. customthe ice bath was removed
  8. additionThe mixture was diluted with water (5 mL)
  9. extractionextracted with dichloromethane (2×10 mL)
  10. dry with materialThe combined organic extracts were dried over magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a7eaaf5f84414eec9e2f4e981112a5e4
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09063126B2

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