Imidazole → HCID 18397574, compound

HRID 1387021Notes

Reaction equation

HRID 1387021 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.C([O-])([O-])=O.[K+].[K+].[CH:12]12[O:18][CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17]2>O>[N:1]1([C@@H:12]2[CH2:17][CH2:16][CH2:15][CH2:14][C@H:13]2[OH:18])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 9246Cyclohexene oxideHCID 11430Potassium Carbonate

Product 1

HCID 18397574HCID 18397574, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 20.18 g of imidazole, 81.95 g of K2CO3, and 20.0 mL of cyclohexene oxide in ca. 200 mL of H2O was stirred at room temperature for 19 h, at 100° C. (bath temp.) for 7 h, and then at room temperature overnight. The mixture was extracted with 3×500 mL of EtOAc and 500 mL of CH2Cl2. The organic layers were washed with 2×300 mL of H2O and 300 mL of brine. Combined organic layers were dried over MgSO4 and concentrated. The crude product was crystallized from EtOAc to yield 8.57 g (26%) of the crystalline solid.

Workup

  1. customat room temperature
  2. customovernight
  3. extractionThe mixture was extracted with 3×500 mL of EtOAc and 500 mL of CH2Cl2
  4. washThe organic layers were washed with 2×300 mL of H2O and 300 mL of brine
  5. dry with materialCombined organic layers were dried over MgSO4
  6. concentrationconcentrated
  7. customThe crude product was crystallized from EtOAc

Sources & evidence

ORD record
ord-2fb2d2f1ac094e47a3a52e7f76a9a609
Source dataset
uspto-grants-2001_07
Patent number
US06265575B1

Reaction notes

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