Dimethylformamide → 4-Bromo-1-(n-butoxymethyl)-2-(p-chlorophenyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile

HRID 1708592

Reaktionsgleichung

[Br:1][C:2]1[C:3]([C:18]#[N:19])=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[NH:5][C:6]=1[C:7]([F:10])([F:9])[F:8].[CH2:20]([O:24][CH2:25]OCCCC)[CH2:21][CH2:22][CH3:23].CN(C)C=O.P(Cl)(Cl)(Cl)=O.C(N(CC)CC)C>O>[Br:1][C:2]1[C:3]([C:18]#[N:19])=[C:4]([C:11]2[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=2)[N:5]([CH2:25][O:24][CH2:20][CH2:21][CH2:22][CH3:23])[C:6]=1[C:7]([F:10])([F:9])[F:8]

Komponenten

Reaktionsbedingungen

Temperatur: 35 °C

Versuchsvorschrift

A stirred mixture of 4-bromo-2- (p-chlorophenyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile (17.4 g, 0.05 mole), di-(n-butoxy)methane (12.0 g, 0.075 mole and dimethylformamide (DMF) (4.6 g, 0.063 mole) in xylenes, under N2, is treated with phosphorous oxychloride (9.6 g, 0.063 mole) portion-wise at 30°-37° C. over a 10 minute period, heated at 45°-50° C. for 0.75 hour, cooled to 35° C., treated dropwise with triethylamine (8.1 g, 0.08 mole) over a 0.25 hour period and heated at 45°-50° C. for an additional 0.75 hour. The reaction mixture is then cooled to 25° C., treated with water and additional xylenes and stirred for 0.5 hour. The phases are separated and the organic phase is concentrated in vacuo to give the title product as a light brown solid, mp 52.0°-53.5° C., 20.6 g, 94.6% yield identified by H1NMR and mass spectral analyses.

Aufarbeitung

temperatureheated at 45°-50° C. for 0.75 hour
temperatureheated at 45°-50° C. for an additional 0.75 hour
temperatureThe reaction mixture is then cooled to 25° C.
customThe phases are separated
concentrationthe organic phase is concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-f65b548425b2479cb151e8d7c0ff8ee7
Quelldatensatz: uspto-grants-1994_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05359090

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