Phosphorus oxychloride → 3-(4-(N-(2-ethylhexyl)-N-propylamino)phenyl)-4-cyano-5-dicyanomethylidene-2-oxo-2,5-dihydropyrrole

HRID 2258368

Reaktionsgleichung

[Na][Na].[C:3]([C:5]1[C:9](=[C:10]([C:13]#[N:14])[C:11]#[N:12])[NH:8][C:7](=[O:15])[C:6]=1O)#[N:4].[CH2:17]([CH:19]([CH2:31][CH2:32][CH2:33][CH3:34])[CH2:20][N:21]([CH2:28][CH2:29][CH3:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH3:18].P(Cl)(Cl)(Cl)=O>CC(C)=O.O.CN(C)C=O>[CH2:17]([CH:19]([CH2:31][CH2:32][CH2:33][CH3:34])[CH2:20][N:21]([C:22]1[CH:23]=[CH:24][C:25]([C:6]2[C:7](=[O:15])[NH:8][C:9](=[C:10]([C:13]#[N:14])[C:11]#[N:12])[C:5]=2[C:3]#[N:4])=[CH:26][CH:27]=1)[CH2:28][CH2:29][CH3:30])[CH3:18]

Komponenten

Reaktionsbedingungen

Temperatur: -10 °C

Versuchsvorschrift

A stirred mixture of disodium salt of 4-cyano-5-dicyanomethylidene-3-hydroxy-2-oxo-2,5-dihydropyrrole (29.9 parts) and dry N,N-dimethylformamide (150 parts) was cooled to -10° C. and N-(2-ethylhexyl)-N-propylaniline containing 30% acetic anhydride (63 parts) was added followed by the dropwise addition of phosphorous oxychloride (34 parts) maintaining the temperature at less than -5°C. The mixture was allowed to warmup to room temperature and stirred for 20 hours. The reaction mixture was poured into a stirred mixture of ice and water (200 parts) and acetone (200 parts) and then stirred for 0.5 hours. The solid was filtered off, washed with hot water and dried under vacuum to give 3-(4-(N-(2-ethylhexyl)-N-propylamino)phenyl)-4-cyano-5-dicyanomethylidene-2-oxo-2,5-dihydropyrrole (48.5 parts, 90%).

Aufarbeitung

temperaturemaintaining the temperature at less than -5°C
customto warmup to room temperature
stirringstirred for 0.5 hours
filtrationThe solid was filtered off
washwashed with hot water
customdried under vacuum

Quellen und Nachweise

ORD-Eintrag: ord-b707bb1bdd8a46fa9be047c3f4b62f7f
Quelldatensatz: uspto-grants-1997_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05660598

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