Urea → 4-(3,5-Bis-trifluoromethylphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid amide

HRID 393683

Reaktionsgleichung

Reaktionsgleichung von HRID 393683
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[CH:6]=O.[C:17]([NH2:23])(=[O:22])[CH2:18][C:19]([CH3:21])=O.[NH2:24][C:25]([NH2:27])=[O:26].B(F)(F)F.CCOCC>[Cu](Cl)Cl.C1COCC1.CC(O)=O>[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([CH:6]2[C:18]([C:17]([NH2:23])=[O:22])=[C:19]([CH3:21])[NH:27][C:25](=[O:26])[NH:24]2)[CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1

Komponenten

8

Edukt 4

HCID 1176UreaHCID 8000Boron trifluoride etherateHCID 80077AcetoacetamideHCID 1362473,5-Bis(trifluoromethyl)benzaldehyde

Produkt 1

HCID 865860054-(3,5-Bis-trifluoromethylphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid amideAusbeute 36,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24014Cupric ChlorideKatalysatorHCID 176Acetic AcidLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

A mixture of 3,5-bis(trifluoromethyl)benzaldehyde (2.42 g, 10.0 mmol), acetoacetamide (1.01 g, 10.0 mmol), urea (0.90 g, 15.0 mmol), copper chloride (0.1 g, 1.0 mmol), boron trifluoride etherate (0.09 mL), AcOH (0.04 mL), and THF (20 mL) was heated at 65° C. for 18 h and cooled to room temperature. The resulting precipitates were collected by vacuum filtration, washed with THF, and air dried to give the title compound as an off-white solid(1.33 g, 36%).

Aufarbeitung

  1. temperaturecooled to room temperature
  2. customThe resulting precipitates
  3. filtrationwere collected by vacuum filtration
  4. washwashed with THF, and air
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-b6dad4d14dd3474a9e23c7ce406e1919
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06809102B2

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