3-Nitrobenzaldehyde → HCID 135833417, Verbindung

HRID 247123

Reaktionsgleichung

Reaktionsgleichung von HRID 247123
[NH2:1][C:2]([CH3:11])=[CH:3][C:4]1[S:8][N:7]=[C:6]([CH2:9][Cl:10])[N:5]=1.[CH2:12]([C:16]1[O:20][N:19]=[C:18]([CH2:21][Cl:22])[N:17]=1)[C:13]([CH3:15])=O.[N+:23]([C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[CH:29]=O)([O-:25])=[O:24]>C(O)(C)C>[CH3:15][C:13]1[NH:1][C:2]([CH3:11])=[C:3]([C:4]2[S:8][N:7]=[C:6]([CH2:9][Cl:10])[N:5]=2)[CH:29]([C:28]2[CH:31]=[CH:32][CH:33]=[C:26]([N+:23]([O-:25])=[O:24])[CH:27]=2)[C:12]=1[C:16]1[O:20][N:19]=[C:18]([CH2:21][Cl:22])[N:17]=1

Komponenten

5

Edukt 3

HCID 74493-NitrobenzaldehydeHCID 138247055-Acetonyl-3-chloromethyl-1,2,4-oxadiazoleHCID 70054050HCID 70054050, Verbindung

Produkt 1

HCID 135833417HCID 135833417, VerbindungAusbeute 15,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

A stirred mixture of 343 mg of 5-(2-amino-1-propenyl)-3-chloromethyl-1,2,4-thiadiazole, 316 mg of 5-acetonyl-3-chloromethyl-1,2,4-oxadiazole and 273 mg of 3-nitrobenzaldehyde in 5 ml of isopropyl alcohol was heated under reflux for 10 hours. The mixture was concentrated in vacuo and the residue was chromatographed on silica gel using benzene-ethyl acetate (5:1) as eluent to give 134 mg of 1,4-dihydro-2,6-dimethyl-3-(3-chloromethyl-1,2,4-oxadiazol-5-yl)-5-(3-chloromethyl-1,2,4-thiadiazol-5-yl)-4-(3-nitrophenyl)pyridine.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 10 hours
  3. concentrationThe mixture was concentrated in vacuo
  4. customthe residue was chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-d2e17b014b244f50b927dd81982f8200
Quelldatensatz
uspto-grants-1987_11
Patentnummer
US04705786

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