Imidazole → HCID 19045277, compound

HRID 1591200Notes

Reaction equation

HRID 1591200 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([OH:12])=[C:7]([C:9](=[O:11])[CH3:10])[CH:8]=1.CN(C)C=O.[Na].[NH:19]1[CH:23]=[CH:22][N:21]=[CH:20]1>>[C:9]([C:7]1[CH:8]=[C:3]([CH2:2][N:19]2[CH:23]=[CH:22][N:21]=[CH:20]2)[CH:4]=[CH:5][C:6]=1[OH:12])(=[O:11])[CH3:10]

Participants

4

Reactant 3

HCID 795ImidazoleHCID 22557013HCID 22557013, compoundHCID 86746767Sodium dimethylformamide

Product 1

HCID 19045277HCID 19045277, compoundYield 33%

Procedure

To a mixture of 5'-(chloromethyl)-2'-hydroxyacetophenone (1.85 g, 10.0 mmol), sodium dimethylformamide was added imidazole (0.75 g, 11.0 mmol). The mixture was stirred four hours and concentrated in vacuo. The residue was stirred under 50 mL ethanol, filtered, and the filtrate concentrated in vacuo to give a residue. The residue was stirred under 30 mL chloroform, filtered, and the filtrate concentrated in vacuo to give crude product. The crude product was purified by flash chromatography eluting with 5:95 methanol:chloroform to give a solid. The solid was recrystallized from n-butlychloride to give 0.71 g (33%) product as a yellow crystalline solid, mp 106°-107° C.

Workup

  1. concentrationconcentrated in vacuo
  2. stirringThe residue was stirred under 50 mL ethanol
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated in vacuo
  5. customto give a residue
  6. stirringThe residue was stirred under 30 mL chloroform
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated in vacuo
  9. customto give crude product
  10. customThe crude product was purified by flash chromatography
  11. washeluting with 5:95 methanol
  12. customchloroform to give a solid
  13. customThe solid was recrystallized from n-butlychloride

Sources & evidence

ORD record
ord-20b3fb84de804f90b4ef99bd61650cba
Source dataset
uspto-grants-1993_04
Patent number
US05206240

Reaction notes

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