Imidazole → N-[2-(7-chlorodibenzofuran-3-yloxy)-ethyl]-imidazole

HRID 615176Notes

Reaction equation

HRID 615176 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]2[C:12]3[CH:13]=[CH:14][C:15]([Cl:17])=[CH:16][C:11]=3[O:10][C:9]=2[CH:18]=1.[NH:19]1[CH:23]=[CH:22][N:21]=[CH:20]1>CN(C)C=O.[I-].[K+]>[Cl:17][C:15]1[CH:14]=[CH:13][C:12]2[C:8]3[CH:7]=[CH:6][C:5]([O:4][CH2:3][CH2:2][N:19]4[CH:23]=[CH:22][N:21]=[CH:20]4)=[CH:18][C:9]=3[O:10][C:11]=2[CH:16]=1

Participants

5

Reactant 2

HCID 795ImidazoleHCID 204295001-Chloro-2-(7-chlorodibenzofuran-3-oxy)-ethane

Product 1

HCID 20429496N-[2-(7-chlorodibenzofuran-3-yloxy)-ethyl]-imidazoleYield 70.4%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

0.5 g of potassium iodide was added to 19.6 g (0.06 mole) of 1-chloro-2-(7-chlorodibenzofuran-3-yloxy)-ethane and 16.4 g (0.24 mole) of imidazole in 50 ml of dimethylformamide, and the mixture was stirred for 16 hours at 110° C., cooled and then evaporated down under reduced pressure. The residue was partitioned between 100 ml of water and 1 liter of methylene chloride, and 20 ml of 50% strength sodium hydroxide solution were added, while cooling with ice. The organic layer was separated off, washed with three times 50 ml of water, dried, and evaporated down under reduced pressure. The solid, colorless residue was left to stand with 15 ml of ether at +5° C. for 1 hour, after which it was filtered off under suction and washed with 20 ml of cold n-pentane. 13.2 g (70.4% of theory) of N-[2-(7-chlorodibenzofuran-3-yloxy)-ethyl]-imidazole of melting point 150°-151° C. were obtained.

Workup

  1. temperaturecooled
  2. customevaporated down under reduced pressure
  3. customThe residue was partitioned between 100 ml of water and 1 liter of methylene chloride, and 20 ml of 50% strength sodium hydroxide solution
  4. additionwere added
  5. temperaturewhile cooling with ice
  6. customThe organic layer was separated off
  7. washwashed with three times 50 ml of water
  8. customdried
  9. customevaporated down under reduced pressure
  10. waitThe solid, colorless residue was left
  11. waitto stand with 15 ml of ether at +5° C. for 1 hour
  12. filtrationafter which it was filtered off under suction
  13. washwashed with 20 ml of cold n-pentane

Sources & evidence

ORD record
ord-d59a60f01acd4c4d826c32135975edc9
Source dataset
uspto-grants-1985_02
Patent number
US04497819

Reaction notes

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