Imidazole → HCID 13520051, compound

HRID 484748Notes

Reaction equation

HRID 484748 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][N:5]=[CH:4]1.[H][H].Cl[CH2:11][C:12]([C:15]1[CH:27]=[CH:26][C:25]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:18][C:17]=2[CH:16]=1)([OH:14])[CH3:13]>O.CN(C)C=O>[N:3]1([CH2:13][C:12]([C:15]2[CH:27]=[CH:26][C:25]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH2:18][C:17]=3[CH:16]=2)([OH:14])[CH3:11])[CH:7]=[CH:6][N:5]=[CH:4]1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 13520052HCID 13520052, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13520051HCID 13520051, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

To a slurry of 743 mg. of a 60% sodium hydride dispersion in oil in 50 ml. of dry dimethylformamide were added, in portions, 2.53 g. of imidazole. After hydrogen evolution had ceased, 3.2 g. of 1-chloro-2-(9H-fluoren-2-yl)-2-propanol in 50 ml. of dry dimethylformamide were added. The mixture was heated to 60° C. for one hour and then stirred overnight at room temperature. After heating an additional 2.5 hours at 85° C., the reaction mixture was poured into 700 ml. of water. The aqueous solution was extracted three times with ethyl acetate. The combined organic extracts were washed first with water followed by a saturated sodium chloride solution wash, dried over sodium sulfate, and evaporated to dryness. The residue was purified by chromatography over silica gel followed by crystallization from tetrahydrofuran/hexanes to provide 1.27 g. of the desired title product, m.p. 183°-184° C.

Workup

  1. temperatureAfter heating an additional 2.5 hours at 85° C.
  2. additionthe reaction mixture was poured into 700 ml
  3. extractionThe aqueous solution was extracted three times with ethyl acetate
  4. washThe combined organic extracts were washed first with water
  5. washwash
  6. dry with materialdried over sodium sulfate
  7. customevaporated to dryness
  8. customThe residue was purified by chromatography over silica gel
  9. customfollowed by crystallization from tetrahydrofuran/hexanes
  10. customto provide 1.27 g

Sources & evidence

ORD record
ord-b190ee44c92a4e44a5300680aaeda2dc
Source dataset
uspto-grants-1985_08
Patent number
US04533670

Reaction notes

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