Hydrochloric Acid → N-ethyl 3-phenylbenzamide

HRID 2421614Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2421614
C[Al](C)C.Cl.[CH2:6]([NH2:8])[CH3:7].[C:9]1([C:15]2[CH:16]=[C:17]([CH:22]=[CH:23][CH:24]=2)[C:18](OC)=[O:19])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl>C1(C)C=CC=CC=1>[CH2:6]([NH:8][C:18](=[O:19])[C:17]1[CH:22]=[CH:23][CH:24]=[C:15]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:16]=1)[CH3:7]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 11198Ethylamine hydrochlorideHCID 9855857Methyl 3-phenylbenzoateHCID 16682925Trimethylaluminum

Produkt 1

HCID 4730715N-ethyl 3-phenylbenzamideAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

Trimethylaluminum (920 μL of 2M solution in toluene, 1.84 mmol) was added drop wise to a suspension of ethylamine hydrochloride (151 mg, 1.84 mmol) in 2.76 mL of dry toluene at 0° C. The reaction was then warmed to room temperature and stirred until no gas evolution was observed. The clear solution was then canulated onto a solution of Methyl 3-phenylbenzoate in 6 mL of toluene. The reaction was then heated to 80° C. and stirred for 18 hours. The reaction mixture was then carefully treated with 5% HCl at 0° C. The aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated. The oil obtained was purified by flash chromatography using SiO2 with CH2Cl2/MeOH 99:1 to give a pale yellow oil (129 mg, 62%). NMR 1H (ppm, CDCl3): 8.0 (s, 1H), 7.72 (d, J3=8.1 Hz, 2H), 7.61 (d, J3=5.4 Hz, 2H), 7.52-7.35 (m, 4H), 6.14 (br. s., 1H), 3.58-3.49 (m, 2H), 1.28 (t, J3=7.5 Hz, 3H).

Aufarbeitung

  1. temperatureThe reaction was then heated to 80° C.
  2. stirringstirred for 18 hours
  3. extractionThe aqueous layer was extracted three times with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe oil obtained
  8. customwas purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d3f480e8763b42a89245363d3544a736
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07956216B2

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