Triethylamine → HCID 22613814, Verbindung

HRID 844576Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 844576
[N:1]1([CH2:6][CH:7]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=2)[CH2:8][CH2:9][O:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)[CH:5]=[CH:4][N:3]=[CH:2]1.C(N(CC)CC)C.[CH3:32][O:33][C:34]1[CH:42]=[CH:41][CH:40]=[CH:39][C:35]=1[C:36](Cl)=[O:37]>C(#N)C>[CH3:32][O:33][C:34]1[CH:42]=[CH:41][CH:40]=[CH:39][C:35]=1[C:36]([C:2]1[N:1]([CH2:6][CH:7]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=2)[CH2:8][CH2:9][O:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)[CH:5]=[CH:4][N:3]=1)=[O:37]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 889692-Methoxybenzoyl chlorideHCID 226138011-(Imidazol-1-yl)-2-(3,4-dichlorophenyl)-4-(tetrahydropyran-2-yloxy)butane

Produkt 1

HCID 22613814HCID 22613814, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

1-(Imidazol-1-yl)-2-(3,4-dichlorophenyl)-4-(tetrahydropyran-2-yloxy)butane (0.86 g) (see Preparation 30) and triethylamine (1.3 ml) were dissolved in acetonitrile (15 ml), under a nitrogen atmosphere, the solution cooled in an ice-bath and 2-methoxybenzoyl chloride (1.4 ml) added, dropwise. The mixture was allowed to warm to room temperature slowly and then stirred for 2 days. The acetonitrile was removed under reduced pressure and the residue dissolved in dichloromethane (20 ml) and washed sequentially with water and brine. The organic phase was then dried over anhydrous sodium sulphate and the solvent removed under reduced pressure to give a residue which was chromatographed on silica gel eluting with 97:3, by volume, dichloromethane:methanol to give 1-[2-(2-methoxybenzoyl)imidazol- 1-yl]-2-(3,4-dichlorophenyl)-4-(tetrahydropyran-2-yloxy)butane (1.1 g) as an oil and as a mixture of diastereomers.

Aufarbeitung

  1. temperaturethe solution cooled in an ice-bath
  2. customThe acetonitrile was removed under reduced pressure
  3. dissolutionthe residue dissolved in dichloromethane (20 ml)
  4. washwashed sequentially with water and brine
  5. dry with materialThe organic phase was then dried over anhydrous sodium sulphate
  6. customthe solvent removed under reduced pressure
  7. customto give a residue which
  8. customwas chromatographed on silica gel eluting with 97:3, by volume, dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-d4d034a2503047a7a17448ae1f2b67a7
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06380396B1

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