Dichloromethane → HCID 22130469, Verbindung

HRID 1857746

Reaktionsgleichung

Reaktionsgleichung von HRID 1857746
[CH2:1]([O:8][CH2:9][C:10]1[NH:11][C:12]([S:18][C:19]2[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([Cl:26])[CH:20]=2)=[C:13]([CH:15]([CH3:17])[CH3:16])[N:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)Cl.[N:30]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:33]=[C:32]([CH2:40]Br)[CH:31]=1.[OH-].[Na+]>O1CCCC1>[CH2:1]([O:8][CH2:9][C:10]1[N:14]([CH2:40][C:32]2[CH:31]=[N:30][C:39]3[C:34]([CH:33]=2)=[CH:35][CH:36]=[CH:37][CH:38]=3)[C:13]([CH:15]([CH3:17])[CH3:16])=[C:12]([S:18][C:19]2[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([Cl:26])[CH:20]=2)[N:11]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 235103313-(Bromomethyl)quinolineHCID 1784190342-Benzyloxymethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1H-imidazole

Produkt 1

HCID 22130469HCID 22130469, VerbindungAusbeute 2,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

In tetrahydrofuran (10 ml) was dissolved 245 mg (2 mmol) of 2-benzyloxymethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1H-imidazole (101a). To this solution, a methylene chloride solution of quinolin-3-ylmethylbromide was added at room temperature with stirring, followed by addition of 200 mg (5 mmol) of sodium hydroxide and 39 mg (0.12 mmol) of n-tetrabutylammonium bromide. After stirring for 2 hours, the mixture was left overnight and worked up. The reaction mixture was distilled off under reduced pressure. The residue was extracted with methylene chloride, and the extract was washed with water and dried. The solvent was distilled off, and the residual oil was purified by silica gel column chromatography (methylene chloride-ethyl acetate). As the first eluate, 26 g (2.6%) of 2-benzyloxymethyl-4-(3,5-dichlorophenylthio)-5-isopropyl-1-(quinolin-3-ylmethyl)-1H-imidazole (100a) was obtained. From the subsequent eluate, 730 mg of 2-benzyloxymethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-(quinolin-3-ylmethyl)-1H-imidazole (100b) suited to the next step of the reaction was obtained (yield 73%).

Aufarbeitung

  1. stirringAfter stirring for 2 hours
  2. distillationThe reaction mixture was distilled off under reduced pressure
  3. extractionThe residue was extracted with methylene chloride
  4. washthe extract was washed with water
  5. customdried
  6. distillationThe solvent was distilled off
  7. customthe residual oil was purified by silica gel column chromatography (methylene chloride-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-e9b74a75c0344ecf922f02f2085e4e1a
Quelldatensatz
uspto-grants-2000_11
Patentnummer
US06147097

Verknüpfte Notizen

Wird geladen…