Dimethylformamide → 7-[(4-chlorophenyl)(isopropyl)amino]-3-(4-methoxybenzyl)-1-methyl-1,3-dihydro-2H-benzimidazol-2-one

HRID 2235554Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2235554
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:14]3[N:15]([CH3:28])[C:16](=[O:27])[N:17]([CH2:18][C:19]4[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=4)[C:13]=3[CH:12]=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.Br[CH:30]([CH3:32])[CH3:31].CN(C)C=O.[H-].[Na+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH:30]([CH3:32])[CH3:31])[C:9]2[C:14]3[N:15]([CH3:28])[C:16](=[O:27])[N:17]([CH2:18][C:19]4[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=4)[C:13]=3[CH:12]=[CH:11][CH:10]=2)=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 63582-BromopropaneHCID 24758Sodium hydrideHCID 685810534-[(4-chlorophenyl)amino]-1-(4-methoxybenzyl)-3-methyl-1,3-dihydro-2H-benzimidazol-2-one

Produkt 1

HCID 685813547-[(4-chlorophenyl)(isopropyl)amino]-3-(4-methoxybenzyl)-1-methyl-1,3-dihydro-2H-benzimidazol-2-oneAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a mixture of 7-[(4-chlorophenyl)amino]-3-(4-methoxybenzyl)-1-methyl-1,3-dihydro-2H-benzimidazol-2-one (0.118 g, 0.30 mmol), 2-bromopropane (0.056 ml, 0.60 mmol), tetrabutylammonium iodide (small amounts) and N,N-dimethylformamide (2 ml) was added sodium hydride (16 mg, 0.60 mmol, 90% dry). The mixture was stirred at 60° C. for 6 h. The mixture was diluted with water (20 ml) and extracted with ethyl acetate (40 ml). The extract was washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue was flash chromatographed with 20-33% ethyl acetate/hexanes to give 80.6 mg (62%) of the title compound as an oil.

Aufarbeitung

  1. extractionextracted with ethyl acetate (40 ml)
  2. washThe extract was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customchromatographed with 20-33% ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-f004aa2b146e4845b0f68f75d23c8797
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07714009B2

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