p-Toluenesulfonic acid monohydrate → 2-(4-Fluoro-3-nitrophenyl)benzoxazole

HRID 74174

Reaktionsgleichung

Reaktionsgleichung von HRID 74174
[F:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([N:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[OH:21])C2C=CC=CC=2)=O)=[CH:4][C:3]=1[N+:24]([O-:26])=[O:25].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]2[O:21][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[N:8]=2)=[CH:4][C:3]=1[N+:24]([O-:26])=[O:25]

Komponenten

4

Edukt 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 674979344-fluoro-N-(2-hydroxyphenyl)-3-nitrobenzanilide

Produkt 1

HCID 219909702-(4-Fluoro-3-nitrophenyl)benzoxazoleAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a suspension of 4-fluoro-N-(2-hydroxyphenyl)-3-nitrobenzanilide (see Working Example 15-1) (2.00 g, 7.24 mmol) in toluene (50 mL) was added p-toluenesulfonic acid monohydrate (2.07 g, 10.9 mmol), and this was stirred and heated to reflux for 4 hours. After the reaction was complete, this was cooled to room temperature, and after the solvent was distilled off, saturated aqueous sodium hydrogen carbonate solution was added and this was stirred for 10 minutes at room temperature. The precipitated crystals were filtered off, and after washing with toluene the crystals were dried to yield the title compound (1.30 g, 70% yield) as yellow crystals.

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux for 4 hours
  3. distillationafter the solvent was distilled off
  4. additionsaturated aqueous sodium hydrogen carbonate solution was added
  5. stirringthis was stirred for 10 minutes at room temperature
  6. filtrationThe precipitated crystals were filtered off
  7. washafter washing with toluene the crystals
  8. customwere dried

Quellen und Nachweise

ORD-Eintrag
ord-503ce20e388a4567b250d68b7b8a3fa5
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829035B2

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