N,N,N',N'-Tetramethylethylenediamine → 1-[4,5-bis(4-methoxyphenyl)-1-(alpha-ethoxyethyl)-1H-imidazol-2-yl]2,2,2-trifluoro-1-ethanone

HRID 1758254Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1758254
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[CH:11][N:12]([CH:22]([O:24][CH2:25][CH3:26])[CH3:23])[C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.CN(C)CCN(C)C.C([Li])CCC.CN(C)[C:42](=[O:47])[C:43]([F:46])([F:45])[F:44].C(=O)(O)[O-].[Na+]>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:10]=[C:11]([C:42](=[O:47])[C:43]([F:46])([F:45])[F:44])[N:12]([CH:22]([O:24][CH2:25][CH3:26])[CH3:23])[C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:7][CH:8]=1

Komponenten

7

Edukt 5

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 3504912,2,2-Trifluoro-N,N-dimethylacetamideHCID 516892Sodium BicarbonateHCID 204060854,5-Bis(4-methoxyphenyl)-1-(alpha-ethoxyethyl)imidazoleHCID 178418339Butyllithium

Produkt 1

HCID 131272901-[4,5-bis(4-methoxyphenyl)-1-(alpha-ethoxyethyl)-1H-imidazol-2-yl]2,2,2-trifluoro-1-ethanoneAusbeute 50,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a stirred solution of 14.12 g (40 mmoles) 4,5-bis(4-methoxyphenyl)-1-(α-ethoxyethyl)imidazole and 4.64 g tetramethylethylenediamine in 100 ml of dry THF under an atmosphere of nitrogen and cooled at -78° was added dropwise 30 ml of 1.6 M n-butyl lithium solution. After stirring for 15 minutes, a solution of 5.7 g (40.1 mmoles) N,N-dimethyltrifluoroacetamide in 30 ml of dry THF was added dropwise. After the addition was complete, the reaction mixture was stirred for 1 hour, with continued cooling, and then 150 ml of a saturated aqueous sodium bicarbonate solution was added dropwise. The mixture was allowed to warm to room temperature. The THF was removed by evaporation under vacuo on a rotary evaporator. The organic components were then extracted with 400 ml of methylene chloride, washed with 100 ml of a saturated solution of sodium bicarbonate, followed by water, and the organic extract was dried over magnesium sulfate. The inorganic salts were removed by filtration, and the solvent was removed by evaporation. The residue was chromatographed on a column of 250 g silica gel, eluting with a solvent mixture consisting of 90 parts toluene and 10 parts ethyl acetate. The chromatographed product thus obtained was crystallized from methyl cyclohexane to give 9 g of 1-[ 4,5-bis(4-methoxyphenyl)-1-(α-ethoxyethyl)-1H-imidazol-2-yl]2,2,2-trifluoro-1-ethanone, m.p. 124°-126°. Infrared and NMR spectra were consistent with the assigned structure.

Aufarbeitung

  1. additionAfter the addition
  2. stirringthe reaction mixture was stirred for 1 hour, with continued cooling
  3. customThe THF was removed by evaporation under vacuo on a rotary evaporator
  4. extractionThe organic components were then extracted with 400 ml of methylene chloride
  5. washwashed with 100 ml of a saturated solution of sodium bicarbonate
  6. extractionthe organic extract
  7. dry with materialwas dried over magnesium sulfate
  8. customThe inorganic salts were removed by filtration
  9. customthe solvent was removed by evaporation
  10. customThe residue was chromatographed on a column of 250 g silica gel
  11. washeluting with a solvent mixture
  12. customThe chromatographed product thus obtained
  13. customwas crystallized from methyl cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-fb17def4d11d4b40be05f7e4535760b8
Quelldatensatz
uspto-grants-1983_02
Patentnummer
US04372964

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