Benzoyl chloride, 3,4,5-trimethoxy- → (2-(Phenylamino)-1-trityl-1H-imidazol-4-yl)(3,4,5 trimethoxyphenyl)methanone

HRID 70055

Reaktionsgleichung

Reaktionsgleichung von HRID 70055
[Li]C(C)(C)C.[C:6]1([NH:12][C:13]2[N:14]([C:18]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:15]=[CH:16][N:17]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH3:37][O:38][C:39]1[CH:40]=[C:41]([CH:45]=[C:46]([O:50][CH3:51])[C:47]=1[O:48][CH3:49])[C:42](Cl)=[O:43]>C1COCC1>[C:6]1([NH:12][C:13]2[N:14]([C:18]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH:15]=[C:16]([C:42]([C:41]3[CH:45]=[C:46]([O:50][CH3:51])[C:47]([O:48][CH3:49])=[C:39]([O:38][CH3:37])[CH:40]=3)=[O:43])[N:17]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Komponenten

5

Edukt 3

HCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 66794278N-Phenyl-1-trityl-1H-imidazol-2-amineHCID 178418306HCID 178418306, Verbindung

Produkt 1

HCID 66780583(2-(Phenylamino)-1-trityl-1H-imidazol-4-yl)(3,4,5 trimethoxyphenyl)methanoneAusbeute 43,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

At −78° C., t-BuLi in THF (1.7 M, 0.34 mL, 0.58 mmol) was added to a solution of trityl protected compound (d) (116 mg, 0.289 mmol) in THF. Then 3,4,5-trimethoxybenzoyl chloride (66.5 mg, 0.289 mmol) was added and stirred overnight. The reaction mixture was quenched with saturated NR4Cl, and dried with MgSO4. Filtration and evaporation of the solvent followed by chromatography afforded compound (e) (75 mg, 43.7%). 1H NMR (500 MHz, CDCl3) δ 7.55-7.41 (m, 5H), 7.32 (s, 1H), 7.28-7.18 (m, 15H), 6.94 (s, 2H), 3.78 (s, 6H), 3.70 (s, 3H). MS: 594.2 (M−H)−; 596.3 (M+H)+.

Aufarbeitung

  1. customThe reaction mixture was quenched with saturated NR4Cl
  2. dry with materialdried with MgSO4
  3. filtrationFiltration and evaporation of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-a52012a079dc464ba99b862016fe9c37
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822513B2

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