Delta-Valerolactone → HCID 12365950, Verbindung

HRID 2398047

Reaktionsgleichung

Reaktionsgleichung von HRID 2398047
[C:1]1(=O)O[CH2:5][CH2:4][CH2:3][CH2:2]1.S(Cl)(Cl)=O.ClC(C)CCC(Cl)=O.[Cl:20][C:21]1[CH:30]=[C:25]([C:26]([NH:28][OH:29])=[O:27])[C:24]([OH:31])=[CH:23][CH:22]=1>[Cl-].[Zn+2].[Cl-]>[Cl:20][C:21]1[CH:22]=[CH:23][C:24]2[O:31][CH:1]3[CH2:2][CH2:3][CH:4]([CH3:5])[O:29][N:28]3[C:26](=[O:27])[C:25]=2[CH:30]=1

Komponenten

6

Edukt 4

HCID 10953Delta-ValerolactoneHCID 24386Thionyl ChlorideHCID 169935Benzamide, 5-chloro-N,2-dihydroxy-HCID 126039624-Chloropentanoyl chloride

Produkt 1

HCID 12365950HCID 12365950, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3007855ZincchlorideKatalysator

Versuchsvorschrift

A mixture of 30 g. of γ -valerolactone, 30 ml. of distilled thionyl chloride and 0.5 g. of zinc chloride was heated on a steam bath overnight and then distilled at 15 mm. The distillate was redistilled at 69- 70° and 15 mm. giving 34 g. of 4-chlorovaleryl chloride. The acid chloride was reduced catalytically, reacted with 5-chlorosalicylhydroxamic acid and the resulting intermediate was ring-closed according to the method described in Example 3. The product after recrystallization from trichloroethylene weighed 8.5 g. and melted at 210- 213° C.

Aufarbeitung

  1. additionA mixture of 30 g
  2. distillationdistilled at 15 mm
  3. distillationThe distillate was redistilled at 69- 70°
  4. customgiving 34 g
  5. customthe resulting intermediate was ring-closed
  6. customThe product after recrystallization from trichloroethylene

Quellen und Nachweise

ORD-Eintrag
ord-c9f79d7b0bf3447899fe351abbbcff38
Quelldatensatz
uspto-grants-1977_05
Patentnummer
US04024139

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