(4-Chlorophenoxy)acetic acid → 2-(4-chlorophenoxy)-N-[5-(imidazol-1-yl)pentyl]acetamide

HRID 323939

Reaktionsgleichung

Reaktionsgleichung von HRID 323939
C(N1C=CN=C1)(N1C=CN=C1)=O.[Cl:13][C:14]1[CH:24]=[CH:23][C:17]([O:18][CH2:19][C:20]([OH:22])=O)=[CH:16][CH:15]=1.[NH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][N:31]1[CH:35]=[CH:34][N:33]=[CH:32]1>C1COCC1>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([O:18][CH2:19][C:20]([NH:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][N:31]2[CH:35]=[CH:34][N:33]=[CH:32]2)=[O:22])=[CH:23][CH:24]=1

Komponenten

5

Edukt 3

HCID 26229(4-Chlorophenoxy)acetic acidHCID 682631,1'-CarbonyldiimidazoleHCID 71384341H-Imidazole-1-pentanamine

Produkt 1

HCID 183497712-(4-chlorophenoxy)-N-[5-(imidazol-1-yl)pentyl]acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

1,1′-Carbonyldiimidazole (6.48 g) was added to a solution of 4-chlorophenoxyacetic acid (7.46 g) in THF (144 ml) at ambient temperature. The mixture was stirred for 2 hours and then 1-(5-aminopentyl)imidazole (6.1 g) was added. The mixture was stirred at ambient temperature for 18 hours and then worked up as described in Example 9a to give an oil which was purified by flash chromatography on silica using ethyl acetate/methanol/ triethylamine, 18:2:1 as the mobile phase to give 2-(4-chlorophenoxy)-N-[5-(imidazol-1-yl)pentyl]acetamide as an oil.

Aufarbeitung

  1. stirringThe mixture was stirred at ambient temperature for 18 hours
  2. customto give an oil which
  3. customwas purified by flash chromatography on silica

Quellen und Nachweise

ORD-Eintrag
ord-53158ecae5aa44cc96315a2a7db6312d
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06215001B1

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