Imidazole → HCID 14349376, compound

HRID 868525Notes

Reaction equation

HRID 868525 reaction equation
S(Cl)(Cl)=O.[NH:5]1[CH:9]=[CH:8][N:7]=[CH:6]1.[CH3:10][C:11]([C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1[OH:20])=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl.O>[OH:20][C:14]1[CH:15]=[CH:16][C:17]([F:19])=[CH:18][C:13]=1[C:11]([N:5]1[CH:9]=[CH:8][N:7]=[CH:6]1)=[CH2:10]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 24386Thionyl ChlorideHCID 959922-Acetyl-4-fluorophenolHCID 516892Sodium Bicarbonate

Product 1

HCID 14349376HCID 14349376, compoundYield 18.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

Thionyl chloride (17.8 g, 0.15 mole) was added dropwise over 30 minutes to 1H-imidazole (41.1 g, 0.60 mole) in dried methylene chloride (200 ml) with stirring and ice-cooling. After stirring for additional 30 minutes, 2-hydroxy-5-fluoroacetophenone (15.4 g, 0.10 mole) in dried methylene chloride (50 ml) was added dropwise over 30 minutes. After stirring for 1 hour, methylene chloride (200 ml), water (400 ml) and an aqueous saturated solution of sodium bicarbonate (200 ml) were added to the reaction mixture and the mixture was stirred for 5 minutes. Then, the organic layer was separated, washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was recrystallized from ethyl acetate to obtain the title compound (3.71 g, 18.2%), m.p. 164°-166° C.

Workup

  1. temperatureice-cooling
  2. stirringAfter stirring for additional 30 minutes
  3. stirringAfter stirring for 1 hour
  4. stirringthe mixture was stirred for 5 minutes
  5. customThen, the organic layer was separated
  6. washwashed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customthe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-68daeceffc5445c18425a8b1c4925419
Source dataset
uspto-grants-1988_10
Patent number
US04780471

Reaction notes

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