Chloroform → 4-[2-(1H-Imidazol-1-yl)ethoxy]aniline

HRID 745920Notes

Reaction equation

HRID 745920 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][C:7]([O:8][CH2:9][CH2:10][N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)=[CH:6][CH:5]=1)([O-])=O.[OH-].[Na+].C(Cl)(Cl)Cl>Cl.[Fe]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([O:8][CH2:9][CH2:10][N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)=[CH:16][CH:17]=1

Participants

6

Reactant 3

HCID 6212ChloroformHCID 14798Sodium HydroxideHCID 135691861-(2-(P-NO2Phenoxy)ethyl)imidazole

Product 1

HCID 135692034-[2-(1H-Imidazol-1-yl)ethoxy]anilineYield 69.8%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 313Hydrochloric AcidSolvent

Procedure

Iron powder (6.0 g) was added in portions to a warm solution of 1-[2-(4-nitrophenoxy)ethyl]imidazole (3.7 g) in 5N hydrochloric acid (60 ml). After 20 minutes the solution was cooled, made basic with dilute sodium hydroxide solution and the mixture was shaken with chloroform and filtered. The chloroform layer of the filtrate was separated, dried (Na2SO4) and evaporated to give a solid which was crystallised from ethyl acetate/petrol to give 1-[2-(4-aminophenoxy)ethyl]imidazole (2.25 g) m.p. 91°-92° C. Found: C, 64.35; H, 6.40; N, 20.61. C11H13N3O requires: C, 65.01; H, 6.45; N, 20.68%.

Workup

  1. temperatureAfter 20 minutes the solution was cooled
  2. filtrationfiltered
  3. customThe chloroform layer of the filtrate was separated
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customto give a solid which
  7. customwas crystallised from ethyl acetate/petrol

Sources & evidence

ORD record
ord-e120851c054a4fa7bafd924510b2f122
Source dataset
uspto-grants-1986_07
Patent number
US04602016

Reaction notes

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