2-Chlorobenzoxazole → N2-(4-bromo-2-fluorophenyl)-1,3-benzoxazol-2-amine

HRID 432381

Reaktionsgleichung

Reaktionsgleichung von HRID 432381
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([F:9])[CH:3]=1.Cl[C:11]1[O:12][C:13]2[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=2[N:15]=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:11]2[O:12][C:13]3[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=3[N:15]=2)=[C:4]([F:9])[CH:3]=1

Komponenten

4

Edukt 2

HCID 119862-ChlorobenzoxazoleHCID 1230504-Bromo-2-fluoroaniline

Produkt 1

HCID 22346948N2-(4-bromo-2-fluorophenyl)-1,3-benzoxazol-2-amineAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of 4-bromo-2-fluoroaniline (1.00 g, 5.26 mmol) in toluene (25 mL) was added 2-chlorobenzoxazole (0.66 mL, 5.79 mmol). The purple solution was heated at reflux for 30 min and then at 100° C. for 17 h. The resulting white suspension/purple solution was cooled to room temperature and the precipitate was filtered. The filter cake was washed with five 2-mL portions of heptane to afford N2-(4-bromo-2-fluorophenyl)-1,3-benzoxazol-2-amine (1.480 g, 92%) as a light purple powder. RP-HPLC (25 to 100% CH3CN in 0.1 N aqueous ammonium acetate over 10 min at 1 mL/min using a Hypersil HS C18, 250×4.6 mm column) tr=12.87 min, 97%; m/z 307 (MH+).

Aufarbeitung

  1. temperatureThe purple solution was heated
  2. temperatureat reflux for 30 min
  3. filtrationthe precipitate was filtered
  4. washThe filter cake was washed with five 2-mL portions of heptane

Quellen und Nachweise

ORD-Eintrag
ord-336774dd31da4b438aeac434494f4bda
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06660744B1

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