Hydrochloric Acid → N-(5-Acetylamino-2-methyl-phenyl)-2,2,2-trifluoro-acetamide

HRID 1071525Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1071525
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:15])=[C:6]([NH:8][C:9](=[O:14])[C:10]([F:13])([F:12])[F:11])[CH:7]=1.N1C=CC=CC=1.[C:22](Cl)(=[O:24])[CH3:23].Cl>CCCCCC.C(OCC)(=O)C.C(Cl)Cl>[C:22]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:15])=[C:6]([NH:8][C:9](=[O:14])[C:10]([F:11])([F:12])[F:13])[CH:7]=1)(=[O:24])[CH3:23]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 6367Acetyl chlorideHCID 22393536N-(5-Amino-2-methyl-phenyl)-2,2,2-trifluoro-acetamide

Produkt 1

HCID 22393509N-(5-Acetylamino-2-methyl-phenyl)-2,2,2-trifluoro-acetamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 21226206Ethyl acetate hexaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

N-(5-Amino-2-methyl-phenyl)-2,2,2-trifluoro-acetamide (3.27 gm 14.99 mmol) was taken up on anhydrous DCM (75 mL) and cooled to 0° C. Pyridine (3.56 g, 44.97 mmol, 3.64 mL) was added followed by a slow addition of acetyl chloride (1.18 g, 14.99 mol, 1.07 mL). The reaction was allowed to warm to room temp and stir for 30 min. The reaction mixture poured into 1N HCl and the aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with saturated sodium bicarbonate, water, brine and dried over anhydrous magnesium sulfate. The solution was filtered and the solvent removed under reduced pressure. The product was isolated by flash chromatography. (3:1 hexane/ethyl acetate) Yield 2.93 g. 1H NMR (CDCl3, 300 MHz) δ 2.13 (s, 3H), 2.23 (s, 3H), 7.25 (d, J=9 Hz, 1H), 7.23 (d, J=9 Hz, 1H), 7.61 (s, 1H).

Aufarbeitung

  1. temperatureto warm to room temp
  2. extractionthe aqueous layer was extracted three times with ethyl acetate
  3. washThe combined organic layers were washed with saturated sodium bicarbonate, water, brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe solution was filtered
  6. customthe solvent removed under reduced pressure
  7. customThe product was isolated by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-4e5752271d6745a3873e46d02b71ad4e
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06906067B2

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