3-Nitrobenzaldehyde → 1,4-Dihydro-2,6-dimethyl-3-(3-chloromethyl-1,2,4-oxadiazol-5-yl)-4-(3-nitrophenyl)pyridine-5-carbonitrile

HRID 247117

Reaktionsgleichung

Reaktionsgleichung von HRID 247117
[CH2:1]([C:5]1[O:9][N:8]=[C:7]([CH2:10][Cl:11])[N:6]=1)[C:2]([CH3:4])=O.[N+:12]([C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=O)([O-:14])=[O:13].[NH2:23]/[C:24](/[CH3:28])=[CH:25]\[C:26]#[N:27]>C(O)(C)C>[CH3:4][C:2]1[NH:23][C:24]([CH3:28])=[C:25]([C:26]#[N:27])[CH:18]([C:17]2[CH:20]=[CH:21][CH:22]=[C:15]([N+:12]([O-:14])=[O:13])[CH:16]=2)[C:1]=1[C:5]1[O:9][N:8]=[C:7]([CH2:10][Cl:11])[N:6]=1

Komponenten

5

Edukt 3

HCID 74493-NitrobenzaldehydeHCID 5325263(2Z)-3-Amino-2-butenenitrileHCID 138247055-Acetonyl-3-chloromethyl-1,2,4-oxadiazole

Produkt 1

HCID 1358334431,4-Dihydro-2,6-dimethyl-3-(3-chloromethyl-1,2,4-oxadiazol-5-yl)-4-(3-nitrophenyl)pyridine-5-carbonitrileAusbeute 42,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

A stirred solution of 1.0 g of 5-acetonyl-3-chloromethyl-1,2,4-oxadiazole, 0.95 g of 3-nitrobenzaldehyde and 0.52 g of 3-aminocrotononitrile in 10 ml of isopropyl alcohol was heated under reflux for 4 hours and then concentrated in vacuo. The residue was chromatographed on silica gel using chloroform-methanol (40:1) as eluent to give 0.90 g of 1,4-dihydro-2,6-dimethyl-3-(3-chloromethyl-1,2,4-oxadiazol-5-yl)-4-(3-nitrophenyl)pyridine-5-carbonitrile, m.p. 204.5°-206.5° C.

Aufarbeitung

  1. temperatureunder reflux for 4 hours
  2. concentrationconcentrated in vacuo
  3. customThe residue was chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-c15cf5165f0e472a8c9fc168441ad460
Quelldatensatz
uspto-grants-1987_11
Patentnummer
US04705786

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