Sodium Iodide → 2-[2-Chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-1,2,3,6-tetrahydropyrimidin-1-yl)phenoxy]-2-(methylthio)acetamide

HRID 1354561Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1354561
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[C:8]([F:10])[C:7]([N:11]2[C:16](=[O:17])[CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[N:13]([CH3:22])[C:12]2=[O:23])=[CH:6][C:5]=1[OH:24].[I-].[Na+].Cl[CH:28]([S:32][CH3:33])[C:29]([NH2:31])=[O:30]>O.C(COC)OC>[Cl:3][C:4]1[CH:9]=[C:8]([F:10])[C:7]([N:11]2[C:16](=[O:17])[CH:15]=[C:14]([C:18]([F:20])([F:21])[F:19])[N:13]([CH3:22])[C:12]2=[O:23])=[CH:6][C:5]=1[O:24][CH:28]([S:32][CH3:33])[C:29]([NH2:31])=[O:30]

Komponenten

7

Edukt 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 112677571-methyl-6-trifluoromethyl-3-(4-chloro-2-fluoro-5-hydroxyphenyl)-2,4(1H,3H)-pyrimidinedioneHCID 229383202-Chloro-2-(methylthio)acetamide

Produkt 1

HCID 210719342-[2-Chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-1,2,3,6-tetrahydropyrimidin-1-yl)phenoxy]-2-(methylthio)acetamideAusbeute 78,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

To a mixture of 1.3 g of sodium hydride and 100 ml of dimethoxyethane, 10 g of 2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-1,2,3,6-tetrahydropyrimidin-1-yl)phenol were added at room temperature and stirred for 30 minutes. Then, 2.2 g of sodium iodide and 6.7 g of crude 2-chloro-2-(methylthio)acetamide were added thereto and stirred at room temperature for 3 hours, and water was poured into the reaction mixture. The reaction mixture was extracted with ethyl acetate. The organic layer was washed with aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography (eluent: ethyl acetate) to give 10.2 g of 2-[2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-1,2,3,6-tetrahydropyrimidin-1-yl)phenoxy]-2-(methylthio) acetamide.

Aufarbeitung

  1. additionwere added at room temperature
  2. stirringstirred at room temperature for 3 hours
  3. extractionThe reaction mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with aqueous sodium bicarbonate solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-dcdda0c73d6a4e329aa662799e8a99e9
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07223862B2

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