Sodium hydride → HCID 21393926, Verbindung

HRID 461461

Reaktionsgleichung

Reaktionsgleichung von HRID 461461
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([OH:16])[CH2:10][N:11]1[CH:15]=[CH:14][N:13]=[CH:12]1.[H-].[Na+].Cl[CH2:20][C:21]1[S:22][CH:23]=[CH:24][CH:25]=1>O1CCCC1>[ClH:1].[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([O:16][CH2:20][C:21]1[S:22][CH:23]=[CH:24][CH:25]=1)[CH2:10][N:11]1[CH:15]=[CH:14][N:13]=[CH:12]1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 32238(+-)-alpha-(2,4-Dichlorophenyl)-1H-imidazole-1-ethanolHCID 698302-(Chloromethyl)thiophene

Produkt 1

HCID 21393926HCID 21393926, VerbindungAusbeute 55,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A solution of 1-(2,4-dichloro-phenyl)-2-(1-imidazolyl) ethanol (1.5 g, 5.8mmole) dissolved in dry tetrahydrofuran (10 ml) was added to a stirred suspension of sodium hydride (0.39 g, as 80% dispersion in oil, 16 mmole) in dry tetrahydrofuran (10 ml) and warmed to 70° C for 90 minutes. The mixture was cooled in ice and a solution of 2-chloromethyl-thiophene (1.16 g, 8.8 mmole) in dry tetrahydrofuran was added. The mixture was heated at 70° for 3 hours and allowed to stir at room temperature overnight. The solvent was removed under vacuum and the residue stirred with dry ether (200 ml). The ether solution was filtered through celite and saturated with hydrogen chloride gas to precipitate an oil which was solidified by trituration with ether and ethylacetate. The solid product was collected and recrystallized from a mixture of acetone and di-isopropyl ether to give 1-[2,4-dichloro-β-(2-thienylmethoxy)phenethyl]imidazole hydrochloride as fine white crystals (0.63 g, 31%) m.p. 153°-154° C. (Found: C, 49.2; H, 3.8; N, 7.3. C16H14Cl2N2OS.HCl requires C, 49.3; H, 3.9; N, 7.2%).

Aufarbeitung

  1. temperatureThe mixture was cooled in ice
  2. temperatureThe mixture was heated at 70° for 3 hours
  3. customThe solvent was removed under vacuum
  4. stirringthe residue stirred with dry ether (200 ml)
  5. filtrationThe ether solution was filtered through celite and saturated with hydrogen chloride gas
  6. customto precipitate an oil which
  7. customThe solid product was collected
  8. customrecrystallized from a mixture of acetone and di-isopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-9d7474e7f621458da5add39693f6cf87
Quelldatensatz
uspto-grants-1977_12
Patentnummer
US04062966

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