Phenol → 3-(4-chlorophenoxy)-N-[3-(imidazol-1-yl)propyl]propionamide

HRID 2268227

Reaction equation

HRID 2268227 reaction equation
[Cl:1][C:2]1[CH:13]=[CH:12][C:5]([O:6][CH2:7][CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.ClC1C=CC(O)=CC=1.C1(O)C=CC=CC=1.O(CCC(O)=O)C1C=CC=CC=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:53][CH2:54][CH2:55][CH2:56][N:57]1[CH:61]=[CH:60][N:59]=[CH:58]1>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][CH2:8][C:9]([NH:53][CH2:54][CH2:55][CH2:56][N:57]2[CH:61]=[CH:60][N:59]=[CH:58]2)=[O:11])=[CH:12][CH:13]=1

Participants

8

Reactant 6

HCID 996PhenolHCID 46844-ChlorophenolHCID 682631,1'-CarbonyldiimidazoleHCID 767803-(4-Chlorophenoxy)propionic acidHCID 787361H-Imidazole-1-propanamineHCID 815963-Phenoxypropionic acid

Product 1

HCID 183498083-(4-chlorophenoxy)-N-[3-(imidazol-1-yl)propyl]propionamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-(4-chlorophenoxy)propionic acid (5.0 g, prepared from 4-chlorophenol by the process described in J.A.C.S. 1923, 2708 for the conversion of phenol into 3-phenoxypropionic acid) in THF (90 ml) was treated with 1,1′-carbonyldiimidazole (4.05 g) at room temperature with stirring. The mixture was stirred at ambient temperature for two hours. 1-(3-Aminopropyl)imidazole (3.12 g) was added and the mixture was stirred at ambient temperature for 18 hours. The solvent was distilled off and the residue was dissolved in dichloromethane, washed with water, dried and then evaporated to give a solid which was recrystallised from ethyl acetate to give 3-(4-chlorophenoxy)-N-[3-(imidazol-1-yl)propyl]propionamide, m.p. 114-115.5° C.

Workup

  1. stirringThe mixture was stirred at ambient temperature for two hours
  2. stirringthe mixture was stirred at ambient temperature for 18 hours
  3. distillationThe solvent was distilled off
  4. dissolutionthe residue was dissolved in dichloromethane
  5. washwashed with water
  6. customdried
  7. customevaporated
  8. customto give a solid which
  9. customwas recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-ebe8e3f338d8429a85a24e10eb934ecf
Source dataset
uspto-grants-2001_12
Patent number
US06326500B1

Linked notes

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