Acetone Cyanohydrin → 3-(4-Chloro-2-nitrobenzoyl)-6,6-dimethylpiperidine-2,4-dione

HRID 1196407

Reaktionsgleichung

Reaktionsgleichung von HRID 1196407
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1.[CH3:14][C:15]1([CH3:23])[NH:20][C:19](=[O:21])[CH2:18][C:17](=[O:22])[CH2:16]1.C(N(CC)CC)C.CC(C)(O)C#N>ClCCl>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([CH:18]2[C:17](=[O:22])[CH2:16][C:15]([CH3:23])([CH3:14])[NH:20][C:19]2=[O:21])=[O:7])=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1

Komponenten

6

Edukt 4

HCID 6406Acetone CyanohydrinHCID 8471Triethylamine2×HCID 108677844-Chloro-2-nitrobenzoyl chlorideHCID 126955936,6-Dimethylpiperidine-2,4-dione

Produkt 1

HCID 198981913-(4-Chloro-2-nitrobenzoyl)-6,6-dimethylpiperidine-2,4-dioneAusbeute 62,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of 4-chloro-2-nitrobenzoyl chloride (4.4 g) in dry dichloromethane (5 ml) was added at 5°-10° C. to a stirred solution of 6,6-dimethylpiperidine-2,4-dione (2.8 g) and triethylamine (2.8 ml) in dry dichloromethane (50 ml) and the mixture was stirred at ambient temperature for 18 hours. Triethylamine (8.4 ml) and acetone cyanohydrin (0.4 ml) were added successively to the solution and the mixture was stirred at ambient temperature for 4 hours. The resulting solution was washed successively with 2N hydrochloric acid (25 ml) and water (3×25 ml), dried over sodium sulphate and evaporated under reduced pressure to give a yellow solid which was recrystallised from acetonitrile to give 3-(4-chloro-2-nitrobenzoyl)-6,6-dimethylpiperidine-2,4-dione (4 g), mp 162°-162.5° C., as a yellow crystalline solid.

Aufarbeitung

  1. stirringthe mixture was stirred at ambient temperature for 4 hours
  2. washThe resulting solution was washed successively with 2N hydrochloric acid (25 ml) and water (3×25 ml)
  3. dry with materialdried over sodium sulphate
  4. customevaporated under reduced pressure
  5. customto give a yellow solid which
  6. customwas recrystallised from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-cce4e7944be34b27b9fe87c1ed71c64c
Quelldatensatz
uspto-grants-1992_05
Patentnummer
US05114461

Verknüpfte Notizen

Wird geladen…