Ethyl Acetate → HCID 10612329, Verbindung

HRID 977189Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 977189
[CH2:1]([C:8]([NH:10][C:11]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]=1[CH2:18][OH:19])=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.C(OCC)(=O)C>ClCCl>[CH2:1]([C:8]([NH:10][C:11]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]=1[CH:18]=[O:19])=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 10707574N-(Benzylcarbonyl)-5-chloro-2-hydroxymethylanilineHCID 178418287HCID 178418287, Verbindung

Produkt 1

HCID 10612329HCID 10612329, VerbindungAusbeute 68,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of N-(benzylcarbonyl)-5-chloro-2-hydroxymethyl aniline (15.50 g) in dichloromethane (400 ml) under nitrogen at room temperature, was added pyridinium chlorochromate (24.30 g) and crushed 4 Å molecular sieves (0.50 g). The reaction mixture was stirred at room temperature for 90 mins, then ethyl acetate added, and the solution was filtered through a 2 inch plug of silica gel. The solvent was removed in vacuo and the material was redissolved in ethyl acetate and filtered through silica gel. Removal of the solvent under vacuum and trituration of the solid residue with diethyl ether gave the desired compound (10.50 g). δ (360 MHz, DMSO-d6) 3.82 (2H, s, NHCOCH2Ph), 7.27-7.39 (6H, m, Ph+5-H), 7.87 (1H, d, J=8.30 Hz, 6-H), 8.36 (1H, d, J=1.87 Hz, 3-H), 9.89 (1H, s, CHO), 10.97 (1H, bs, NHCOCH2Ph).

Aufarbeitung

  1. customcrushed 4 Å molecular sieves (0.50 g)
  2. filtrationthe solution was filtered through a 2 inch plug of silica gel
  3. customThe solvent was removed in vacuo
  4. dissolutionthe material was redissolved in ethyl acetate
  5. filtrationfiltered through silica gel
  6. customRemoval of the solvent under vacuum and trituration of the solid residue with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-4a4ac8c0406942d3add6dd31bb6ab18a
Quelldatensatz
uspto-grants-1997_03
Patentnummer
US05614532

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