Benzene → N-(4-fluoro-alpha,alpha-dimethylbenzyl)-o-methylphenylacetamide

HRID 1980056

Reaktionsgleichung

Reaktionsgleichung von HRID 1980056
C1C=CC=CC=1.[F:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([NH2:15])([CH3:14])[CH3:13])=[CH:10][CH:9]=1.[CH3:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH2:25][C:26](Cl)=[O:27]>C(N(CC)CC)C>[F:7][C:8]1[CH:9]=[CH:10][C:11]([C:12]([NH:15][C:26](=[O:27])[CH2:25][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[CH3:18])([CH3:14])[CH3:13])=[CH:16][CH:17]=1

Komponenten

5

Edukt 3

HCID 241BenzeneHCID 2760632o-Tolyl-acetyl chlorideHCID 130256652-(4-Fluorophenyl)propan-2-amine

Produkt 1

HCID 12790296N-(4-fluoro-alpha,alpha-dimethylbenzyl)-o-methylphenylacetamideAusbeute 78,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

Into a 300 ml four-necked flask, there were charged benzene (200 ml), 4-fluoro-α,α-dimethylbenzylamine (7.7 g) and triethylamine (6.0 g), and o-methylphenylacetyl chloride (9.5 g) was dropwise added thereto at room temperature while stirring, followed by refluxing for 3 hours. After cooling, the reaction mixture was washed with water to remove triethylamine hydrochloride. After the benzene layer was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The residue was recrystallized from ethanol to give 11.3 g of N-(4-fluoro-α,α-dimethylbenzyl)-o-methylphenylacetamide (Compound No. 11). M.P., 150°-151° C.

Aufarbeitung

  1. additionwas dropwise added
  2. temperatureby refluxing for 3 hours
  3. temperatureAfter cooling
  4. washthe reaction mixture was washed with water
  5. customto remove triethylamine hydrochloride
  6. dry with materialAfter the benzene layer was dried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-18fc235c6aba47319e43615affca2fd3
Quelldatensatz
uspto-grants-1984_11
Patentnummer
US04484942

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