p-Toluenesulfonic acid → HCID 178498285, Verbindung

HRID 349496

Reaktionsgleichung

Reaktionsgleichung von HRID 349496
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:12][O:13][C:14](=[O:24])[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([NH2:23])[CH:16]=1.[Cl:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][C:33]=1[F:34])[C:29]#[N:30].C([O-])(O)=O.[Na+]>>[CH3:12][O:13][C:14](=[O:24])[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([NH:23][C:29](=[NH:30])[C:28]2[CH:31]=[CH:32][C:33]([F:34])=[C:26]([Cl:25])[CH:27]=2)[CH:16]=1

Komponenten

5

Edukt 4

HCID 6101p-Toluenesulfonic acidHCID 1455253-Chloro-4-fluorobenzonitrileHCID 516892Sodium BicarbonateHCID 2734814Methyl 3-Amino-4-methoxybenzoate

Produkt 1

HCID 178498285HCID 178498285, VerbindungAusbeute 45 %

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

Anhydrous p-toluene sulfonic acid (10 g, 52.57 mmol) was melted at 120° C. and 3-amino-4-methoxy benzoic acid methyl ester (3.88 g, 21.44 mmol) obtained in step 1 of Preparation Example 1 and 3-chloro-4-fluorobenzonitrile (5.0 g, 32.14 mol) were added thereto and stirred at 160° C. for 8 hours. The resulting solution was cooled to room temperature and the reaction was stopped by adding NaHCO3 thereto. The resulting mixture was extracted with ethyl acetate, the extract was dried over MgSO4 and concentrated under a reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound (3.24 g, 9.62 mmol) in a yield of 45%.

Aufarbeitung

  1. additionwere added
  2. temperatureThe resulting solution was cooled to room temperature
  3. extractionThe resulting mixture was extracted with ethyl acetate
  4. dry with materialthe extract was dried over MgSO4
  5. concentrationconcentrated under a reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-0f3630fd6bd54e7a832327e814aa6609
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07179832B2

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