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

HRID 378599

Reaction equation

HRID 378599 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-c3c03d208a5246ecb2715e5a5d03c9ef
Source dataset
uspto-grants-2000_02
Patent number
US06031109

Linked notes

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