Hydrochloric Acid → 3-(4-chloro-6-fluoro-3-methyl-2-nitrophenyl)-6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedione

HRID 1271754

Reaktionsgleichung

[NH2:1]/[C:2](/[C:9]([F:12])([F:11])[F:10])=[CH:3]\[C:4]([O:6]CC)=O.N12CCCN=C1CCCCC2.[Cl:24][C:25]1[C:40]([CH3:41])=[C:39]([N+:42]([O-:44])=[O:43])[C:28]([NH:29][C:30](OC2C=CC=CC=2)=[O:31])=[C:27]([F:45])[CH:26]=1.Cl>CN(C)C=O.O>[Cl:24][C:25]1[CH:26]=[C:27]([F:45])[C:28]([N:29]2[C:4](=[O:6])[CH:3]=[C:2]([C:9]([F:10])([F:11])[F:12])[NH:1][C:30]2=[O:31])=[C:39]([N+:42]([O-:44])=[O:43])[C:40]=1[CH3:41]

Komponenten

Reaktionsbedingungen

Temperatur: -10 °C

Versuchsvorschrift

Ethyl 3-amino-4,4,4-trifluorocrotonate (61.3 g, 33.1 mmol) was dissolved in dimethylformamide (47 ml) and stirred at −10 ° C. To this solution was slowly added 1,8-diazabicyclo [5.4.0]undec-7-ene (6.3 g, 41.4 mmol) and solution stirred for 0.5 hr. To this solution was slowly added a solution of 4-chloro-2-fluoro-5-methyl-6-nitro-N-phenoxycarbonylaniline (8.5 g) in dimethylformamide (25 ml) followed by stirring at ambient temperature for 14 hr. Solution was then heated to 80 ° C. and stirred at this temperature for 4 hr. Water was added and pH adjusted to 4 by addition of dilute hydrochloric acid. Product was extracted with ethyl acetate followed by evaporation of the solvent to afford the crude product (10.1 g) which was subjected to N-methylation as follows.

Aufarbeitung

stirringstirred for 0.5 hr
stirringby stirring at ambient temperature for 14 hr
temperatureSolution was then heated to 80 ° C.
stirringstirred at this temperature for 4 hr
extractionProduct was extracted with ethyl acetate
customfollowed by evaporation of the solvent

Quellen und Nachweise

ORD-Eintrag: ord-e9acf5a88dd343febdcfa401ece79eb0
Quelldatensatz: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: USRE039590E1

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