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Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → 7-Fluoro-2-(2-hydroxy-1,1-dimethylethyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

HRID 17354
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 17354
[C:1]([C:3]1[C:4]([CH3:25])=[C:5]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:6]([F:18])=[C:7]([OH:17])[C:8]=1[NH:9][C:10](=O)[C:11]([CH3:15])([CH3:14])[CH2:12][OH:13])#[N:2].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[F:18][C:6]1[C:5]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:4]([CH3:25])[C:3]([C:1]#[N:2])=[C:8]2[C:7]=1[O:17][C:10]([C:11]([CH3:14])([CH3:15])[CH2:12][OH:13])=[N:9]2
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Komponenten

5

Edukt 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 86630840N-(3-Cyano-6-fluoro-5-hydroxy-2-methyl[1,1'-biphenyl]-4-yl)-3-hydroxy-2,2-dimethylpropanamide

Produkt 1

HCID 685859577-Fluoro-2-(2-hydroxy-1,1-dimethylethyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrileAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittel
HCID 8857
Ethyl Acetate
Lösungsmittel

Versuchsvorschrift

N-(3-Cyano-6-fluoro-5-hydroxy-2-methyl[1,1′-biphenyl]-4-yl)-3-hydroxy-2,2-dimethylpropanamide (I-98) (184 mg, 0.54 mmol) was dissolved in toluene (3.7 ml), pyridinium p-toluenesulfonate (34 mg, 0.13 mmol) was added, followed by stirring under heat for 15 hours. After cooling to room temperature, this was diluted with ethyl acetate, washed with aqueous sodium hydrogencarbonate solution and saturated brine. The obtained organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated away under reduced pressure. The resulting residue was recrystallized and purified with diisopropyl ether/ethyl acetate to obtain the entitled compound (118.6 mg, 68%) as a white solid.

Aufarbeitung

  1. temperatureunder heat for 15 hours
  2. washwashed with aqueous sodium hydrogencarbonate solution and saturated brine
  3. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated away under reduced pressure
  5. customThe resulting residue was recrystallized
  6. custompurified with diisopropyl ether/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-12851e62832341b3919bbaae660a156f
Quelldatensatz
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07737166B2

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