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

HRID 378599

Reaktionsgleichung

Reaktionsgleichung von HRID 378599
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-c3c03d208a5246ecb2715e5a5d03c9ef
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06031109

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