Aluminum(III) Chloride → N-(1-Oxo-1,2,3,4-tetrahydronaphthalen-2-yl)benzamide

HRID 904816Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 904816
[C:1]([NH:9][C@H:10]([C:19]([OH:21])=O)[CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Al+3].[Cl-].[Cl-].[Cl-]>C(OC(=O)C)(=O)C.C(=S)=S>[C:1]([NH:9][CH:10]1[CH2:11][CH2:12][C:13]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:19]1=[O:21])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 2

HCID 6451240Aluminum(III) ChlorideHCID 22824842HCID 22824842, Verbindung

Produkt 1

HCID 13293063N-(1-Oxo-1,2,3,4-tetrahydronaphthalen-2-yl)benzamideAusbeute 817,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6348Carbon DisulfideLösungsmittelHCID 7918Acetic AnhydrideLösungsmittel

Versuchsvorschrift

A solution of N-benzoyl homophenylalanine (4.4 g, 1.66 mmole) in acetic anhydride (60 ml) was heated on the steam bath for 1/2 hr. The solvent was removed in vacuo, the resulting oil was dissolved in CS2 and then added to a suspension of AlCl3 (6.2 g, 4.6 mmoles) in CS2 (60 ml). This mixture was heated at reflux for 1 hr, the solvent was removed in vacuo and ice was added to the residue. The reaction mixture was extracted with ethyl acetate, the ethyl acetate layer was washed with brine, dried over Na2SO4 and evaporated to dryness to afford 3.6 g (88%) of product, m.p. 175° C. After recrystallization from toluene it had m.p. 175°-178° C.

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. dissolutionthe resulting oil was dissolved in CS2
  3. temperatureThis mixture was heated
  4. temperatureat reflux for 1 hr
  5. customthe solvent was removed in vacuo and ice
  6. additionwas added to the residue
  7. extractionThe reaction mixture was extracted with ethyl acetate
  8. washthe ethyl acetate layer was washed with brine
  9. dry with materialdried over Na2SO4
  10. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-a4a5d12ba0594f4fbf16ba85a740e3aa
Quelldatensatz
uspto-grants-1983_12
Patentnummer
US04420480

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