Dimethylamine → 2-(3-Phenoxybenzoyl)-3-dimethylaminoacrylonitrile

HRID 465273Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 465273
[O:1]([C:8]1[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=1)[C:11]([CH2:13][C:14]#[N:15])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19]OC(OC)OC.[CH3:26][NH:27][CH3:28]>C(O)C>[O:1]([C:8]1[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=1)[C:11]([C:13](=[CH:26][N:27]([CH3:19])[CH3:28])[C:14]#[N:15])=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 674DimethylamineHCID 9005Trimethyl orthoformateHCID 198735383-Phenoxybenzoylacetonitrile

Produkt 1

HCID 540996322-(3-Phenoxybenzoyl)-3-dimethylaminoacrylonitrileAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

3-Phenoxybenzoylacetonitrile (4 g) and trimethylorthoformate (30 ml) was stirred and heated to 80° C. for 2 hours. After cooling to 0° C., an excess of dimethylamine in ethanol solution was added and the mixture stirred for 2 hours at room temperature. The volatiles were then removed in vacuo and the residue chromatographed on a silica gel column using 5% methanol-dichloromethane (v/v) as eluant to give the title compound (3.2 g, 65%) as a white solid of m.p. 80°-82° C.

Aufarbeitung

  1. temperatureAfter cooling to 0° C.
  2. customThe volatiles were then removed in vacuo
  3. customthe residue chromatographed on a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-24c7e09ccf0e45d3b3d029d0a6862cad
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05152825

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