5-Chloro-3,4-diphenyl-1,2-oxazole → HCID 53801427, Verbindung

HRID 343084Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 343084
Cl[C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH3:19][S-:20].[Na+]>CS(C)=O.O>[CH3:19][S:20][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

5

Edukt 2

HCID 2857785-Chloro-3,4-diphenyl-1,2-oxazoleHCID 4378561Sodium methanethiolate

Produkt 1

HCID 53801427HCID 53801427, VerbindungAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a stirred solution of 5-chloro-3,4-diphenylisoxazole (Step 1) (1.75 g, 6.84 mmol) in DMSO (30 mL) was added sodium thiomethoxide (0.58 g, 8.21 mmol). After stirring for 30 hours at room temperature, the reaction was diluted with water and extracted twice with Et2O . The combined ethereal phases were washed with NaHCO3 saturated solution, KHSO4 solution (0.25N), and brine, dried over MgSO4, filtered and concentrated in vacuo yielding 5-methylthio-3,4-diphenylisoxazole (1.53 g, 84%): mp 83°-86° C. 1H NMR (CDCl3 /300 MHz) 7.50-7.18 (m, 10H), 2.63 (s, 3H). FABLRMS m/z 268 (M+H). FABHRMS m/z 268.0781 (M+H C16H14NOS requires 268.0796). Anal. Calc'd for C16H13NOS: C, 71.88; H, 4.90; N, 5.24. Found: C, 71.71; H, 4.95; N, 5.17.

Aufarbeitung

  1. extractionextracted twice with Et2O
  2. washThe combined ethereal phases were washed with NaHCO3 saturated solution, KHSO4 solution (0.25N), and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-2424eca378a64928bcda2c1498ad51e9
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05859257

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