Imidazole → HCID 43162810, compound

HRID 867958Notes

Reaction equation

HRID 867958 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.Br[CH2:7][C:8]([C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=1)=[O:9]>CO.O1CCOCC1.CCOCC>[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:7][C:8]([C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=1)=[O:9]

Participants

6

Reactant 2

HCID 795ImidazoleHCID 691792-Bromo-2'-acetonaphthone

Product 1

HCID 43162810HCID 43162810, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 68.32 g (1.004 mol) of imidazole dissolved in 150 ml of methanol at 0° C. (ice-bath) is added dropwise a solution of 2-bromo-2'-acetonaphthone (50 g, 0.201 mol) in 100 ml of dioxane and 25 ml of ether, while keeping the temperature at 0° C. After about 3 hours at 0° C., the mixture is allowed to warm to room temperature where it is stirred for 20 hours. The mixture is then filtered and added to 500 ml of water, extracted 3 times with 500 ml of chloroform, dried over magnesium sulfate, and evaporated under reduced pressure. The brown oil that remaines is crystallized with a small amount of ethyl acetate and hexane and collected by filtration. The solid is heated in ethyl acetate and filtered hot then concentrated enough to recrystallized the produce as a light tan solid. Yield: 31.07 g (65%); m.p. 125°-126° C. (Found: C, 76.03; H, 5.25; N, 11.81. C15H12N2O requires: C, 76.25; H, 5.12; N, 11.86).

Workup

  1. customat 0° C
  2. filtrationThe mixture is then filtered
  3. additionadded to 500 ml of water
  4. extractionextracted 3 times with 500 ml of chloroform
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under reduced pressure
  7. customThe brown oil that remaines is crystallized with a small amount of ethyl acetate and hexane
  8. filtrationcollected by filtration
  9. temperatureThe solid is heated in ethyl acetate
  10. filtrationfiltered hot
  11. concentrationthen concentrated enough
  12. customto recrystallized the
  13. customproduce as a light tan solid

Sources & evidence

ORD record
ord-892328c8609849f1a60a608d69ef0a97
Source dataset
uspto-grants-1988_10
Patent number
US04777263

Reaction notes

Loading…