Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 68585126, Verbindung

HRID 17507Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 17507
[C:1]1([C:6]([O:8][C:9]2[C:10]([F:25])=[C:11]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:12]([CH3:18])=[C:13]([C:16]#[N:17])[C:14]=2[NH2:15])=O)[CH2:5][CH2:4][CH2:3][CH:2]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C1(C)C(C)=CC=CC=1>[C:1]1([C:6]2[O:8][C:9]3[C:14](=[C:13]([C:16]#[N:17])[C:12]([CH3:18])=[C:11]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[C:10]=3[F:25])[N:15]=2)[CH2:5][CH2:4][CH2:3][CH:2]=1

Komponenten

4

Edukt 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 866308604-Amino-5-cyano-2-fluoro-6-methylbiphenyl-3-yl cyclopentenecarboxylate

Produkt 1

HCID 68585126HCID 68585126, VerbindungAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7237O-XyleneLösungsmittel

Versuchsvorschrift

4-Amino-5-cyano-2-fluoro-6-methylbiphenyl-3-yl cyclopentenecarboxylate (I-213) (180 mg, 0.54 mmol) was dissolved in xylene (50 ml), pyridinium p-toluenesulfonate (50 mg) was added, followed by heating under reflux for 5 hours. After cooling to room temperature, the solvent was evaporated away under reduced pressure. The resulting residue was diluted with ethyl acetate, and washed with saturated brine. The obtained organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated away under reduced pressure. The resulting residue was subjected to silica gel column chromatography, and eluted with a mixed solvent of n-hexane/ethyl acetate (4:1, v/v) to obtain the entitled compound (148 mg, 87%) as a white crystal.

Aufarbeitung

  1. temperatureby heating
  2. temperatureunder reflux for 5 hours
  3. customthe solvent was evaporated away under reduced pressure
  4. additionThe resulting residue was diluted with ethyl acetate
  5. washwashed with saturated brine
  6. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  7. customthe solvent was evaporated away under reduced pressure
  8. washeluted with a mixed solvent of n-hexane/ethyl acetate (4:1

Quellen und Nachweise

ORD-Eintrag
ord-cd068948037a46c1a9ace3ee6761f9ff
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737166B2

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