5-Fluoro-o-tolyl Isothiocyanate → Methyl (2-(5-fluoro-2-methylphenylamino)-7-fluoro-6-benzoxazolyl)acetate

HRID 1372644

Reaktionsgleichung

Reaktionsgleichung von HRID 1372644
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[C:4]([F:13])[C:3]=1[OH:14].[F:15][C:16]1[CH:17]=[CH:18][C:19]([CH3:25])=[C:20]([N:22]=[C:23]=S)[CH:21]=1>CO>[F:15][C:16]1[CH:17]=[CH:18][C:19]([CH3:25])=[C:20]([NH:22][C:23]2[O:14][C:3]3[C:4]([F:13])=[C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:7][C:2]=3[N:1]=2)[CH:21]=1

Komponenten

4

Edukt 2

HCID 5194435-Fluoro-o-tolyl IsothiocyanateHCID 17859032HCID 17859032, Verbindung

Produkt 1

HCID 44607521Methyl (2-(5-fluoro-2-methylphenylamino)-7-fluoro-6-benzoxazolyl)acetateAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

In methanol (30 ml) was dissolved methyl (4-amino-2-fluoro-3-hydroxyphenyl)acetate (1.0 g, 5.02 mmol). To the resulting solution was added 5-fluoro-2-methylphenyl isothiocyanate (1.0 g, 5.98 mmol). After the resulting mixture was stirred at room temperature for 5 days, mercuric oxide (yellow) (1.14 g, 4.36 mmol) was added thereto. The mixture was stirred at 70° C. for 6 hours. After cooling to room temperature, the reaction mixture was filtered through Celite and washed 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 (30/1, v/v) eluate fractions, methyl (2-(5-fluoro-2-methylphenylamino)-7-fluoro-6-benzoxazolyl)acetate (810 mg, 56% (2 steps)) was obtained as a pink solid.

Aufarbeitung

  1. stirringThe mixture was stirred at 70° C. for 6 hours
  2. temperatureAfter cooling to room temperature
  3. filtrationthe reaction mixture was filtered through Celite
  4. washwashed 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 (30/1

Quellen und Nachweise

ORD-Eintrag
ord-672c550ec85c4431afa5341f70e99fc0
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07157487B2

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