1-Bromohexadecane → 4-Hexadecylaminobenzoylacetonitrile

HRID 1702693

Reaktionsgleichung

Reaktionsgleichung von HRID 1702693
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([CH2:8][C:9]#[N:10])=[O:7])=[CH:4][CH:3]=1.Br[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].C(=O)([O-])[O-].[K+].[K+]>CN(C)P(N(C)C)(N(C)C)=O>[CH2:29]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([CH2:8][C:9]#[N:10])=[O:7])=[CH:11][CH:12]=1)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH3:14]

Komponenten

5

Edukt 3

HCID 82131-BromohexadecaneHCID 11430Potassium CarbonateHCID 96920Benzenepropanenitrile, 4-amino-beta-oxo-

Produkt 1

HCID 205258344-Hexadecylaminobenzoylacetonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 12679HexamethylphosphoramideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of p-aminobenzoylacetonitrile, 1-bromohexadecane, potassium carbonate and hexamethylphosphoramide is heated to 80° C. for 20 hours and worked up as in Example 1, providing 4-hexadecylaminobenzoylacetonitrile. This material is dissolved in isopropanol and treated with an excess of sodium borohydride. After stirring at room temperature for 3 hours, the solution is concentrated, diluted with water and extracted with chloroform. The chloroform extract yields the crude carbinol which is heated to reflux for 1 hour with ethanol containing an equal volume of 2 N aqueous hydrochloric acid. The solution is then cooled, diluted with water and extracted with chloroform. The organic extract is washed successively with water and aqueous sodium bicarbonate, then dried and evaporated to afford 4-(hexadecylamino)cinnamonitrile.

Quellen und Nachweise

ORD-Eintrag
ord-6c0f44f169134eb7bf22eae09570c292
Quelldatensatz
uspto-grants-1982_09
Patentnummer
US04348399

Verknüpfte Notizen

Wird geladen…