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

HRID 1956836Notes

Reaction equation

HRID 1956836 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-ffe734f801ec424ebc8f26148ea0c3cc
Source dataset
uspto-grants-1998_07
Patent number
US05780642

Reaction notes

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