5-Fluoro-o-tolyl Isothiocyanate → Methyl (2-(5-fluoro-2-methylphenylamino)-6-benzoxazolyl)acetate

HRID 1372779Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1372779
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([N:8]=[C:9]=S)[CH:7]=1.[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]([O:22][CH3:23])=[O:21])=[CH:15][C:14]=1[OH:24]>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([NH:8][C:9]2[O:24][C:14]3[CH:15]=[C:16]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[CH:17]=[CH:18][C:13]=3[N:12]=2)[CH:7]=1

Komponenten

4

Edukt 2

HCID 5194435-Fluoro-o-tolyl IsothiocyanateHCID 17858854Methyl 2-(4-amino-3-hydroxyphenyl)acetate

Produkt 1

HCID 58778736Methyl (2-(5-fluoro-2-methylphenylamino)-6-benzoxazolyl)acetateAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

In methanol (50 ml), 5-fluoro-2-methylphenyl isothiocyanate (2.00 g, 12.0 mmol) was added to methyl 4-amino-3-hydroxyphenylacetate (2.17 g, 12.0 mmol) and the resulting mixture was stirred at room temperature for 27 hours. Mercuric oxide (yellow) (3.12 g, 14.4 mmol) was added to the reaction mixture, followed by stirring at 70° C. for 4 hours. After cooling to room temperature, the reaction mixture was filtered through Celite, followed by washing with methanol. The filtrate was distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from chloroform/ethyl acetate (10/1) eluate fractions, methyl (2-(5-fluoro-2-methylphenylamino)-6-benzoxazolyl)acetate (1.73 g, 46%) was obtained as a brown oil.

Aufarbeitung

  1. stirringby stirring at 70° C. for 4 hours
  2. temperatureAfter cooling to room temperature
  3. filtrationthe reaction mixture was filtered through Celite
  4. washby washing with methanol
  5. distillationThe filtrate was distilled under reduced pressure
  6. customto remove the solvent
  7. customThe residue was purified by chromatography on a silica gel column, whereby from chloroform/ethyl acetate (10/1) eluate fractions

Quellen und Nachweise

ORD-Eintrag
ord-51240d3978e6424c862d360988afc489
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07157487B2

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